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  • 1.
    Andersson, Claes-Henrik
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Reproducibility and efficiency of carbon nanotube end-group generation and functionalization2009In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 26, p. 4421-4428Article in journal (Refereed)
    Abstract [en]

    In a systematic fashion, several methods for esterification and  amidation of single-walled carbon nanotubes have been evaluated with   focus on efficiency and reproducibility in forming covalently   functionalized products soluble in organic media. The outcome of   transformations was determined using IR, Raman and NMR spectroscopy and   by thermogravimetric analysis (TGA). Amidation proceeding via a   SWNT-(COCl)(n) intermediate yielded the expected covalent product,  whereas carboxylate salt formation dominated with other attempted   methods. Esterification was achieved via the acyl chloride method and   via alkylation of SWNT-(COO-)(n), the latter being the more efficient   method. A non-covalent solubilizing interaction was obtained for RNH2   but not for ROH (R = octadecyl), proving that the most important   non-covalent interaction between oxidatively cleaned SWNTs and   octadecylamine is a salt formation. The outcome of the secondary   functionalization of carboxyl units is highly reproducible for   experiments carried out on the same batch of SWNT-(COOH)(n). Normalization of the outcome of the secondary functionalization to the   composition of the different batches of starting materials reveals an overall high reproducibility of the secondary function alizations. The   differences in outcome related to different commercial SWNT batches   from the same synthetic procedure is negligible compared to that   resulting from differences in overall carboxyl content after the   primary HNO3 oxidative cleaning step. Hence, the composition of   purified SWNT starting materials always needs to be assessed, in particular before drawing any conclusions concerning differences in   outcome from reaction systems involving different sources of SWNT  material.

  • 2.
    Ankner, Tobias
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Norberg, Thomas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Kihlberg, Jan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Mild Oxidative Cleavage of 9-BBN-Protected Amino Acid Derivatives2015In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 17, p. 3767-3770Article in journal (Refereed)
    Abstract [en]

    Protection of the amino acid moiety using 9-BBN is an effective method to enable side chain manipulations in synthesis of complex amino acids. We investigated the standard, mild method for deprotection of the 9-BBN group in methanolic chloroform, and found that it relies on a slow oxidation mediated by molecular oxygen. Building on this insight, we have developed a method that allows for a fast and selective deprotection using simple peroxy acid reagents. After Fmoc protection, products were isolated in >90% yield for a series of amino acid derivatives, including a galactosylated derivative of hydroxylysine.

  • 3.
    Appukkuttan, Prasad
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Van der Eycken, Erik
    Recent developments in microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions2008In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 7, p. 1133-1155Article, review/survey (Refereed)
    Abstract [en]

    A selective over-view of the recent developments of microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions is presented. Microwave-assisted chemistry is a comparatively novel technique in the present-day synthetic world and has recently grown in an exponential manner, stretching from academia to a widely practiced technique in industry. Transition-metal-catalysed C-C and C-N bond-forming reactions represent one of the most interesting and well-investigated type of microwave-assisted reactions, evident from the plethora of available literature and patents in this area. Given the large number of articles published on the subject, we have made a very concise selection from the recent literature, covering manuscripts dealing with the subject from the period of the end 2004 until the first part of 2007.

  • 4.
    Arkhypchuk, Anna I.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Orthaber, Andreas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Kovacs, Daniel
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Borbas, K. Eszter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Isolation and Characterization of a Monoprotonated Hydroporphyrin2018In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 48, p. 7051-7056Article in journal (Refereed)
    Abstract [en]

    A simple protocol for the controlled preparation of mono- and diprotonated hydroporphyrins (chlorins) is presented. The chlorins carried 10-aryl groups with electron-neutral (phenyl), electron-donating (p-OMe-C6H4) or electron-withdrawing (pentafluorophenyl) substituents. The protonation reactions were readily followed by UV/Vis absorption spectroscopy, enabling the determination of the first (4.8-5.3) and second pK(a)'s (1.7-0.5). Both mono- and diprotonated species were fully characterized by H-1 NMR spectroscopy, which, in combination with theoretical studies, showed that these macrocycles were significantly distorted in solution. A 10-phenyl-substituted monoprotonated chlorin was characterized by X-ray crystallography. This is the first structurally characterized hydroporphyrin monocation, and the first crystal structure of a sterically unencumbered singly protonated tetrapyrrole. The photostabilities of the mono- and diprotonated 10-phenylchlorins were measured upon irradiation into their Soret bands; protonation yielded increased photostabilities.

  • 5.
    Belfrage, Anna Karin
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Gising, Johan
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Svensson, Fredrik
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Åkerblom, Eva
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sköld, Christian
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sandström, Anja
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Efficient and Selective Palladium-Catalysed C-3 Urea Couplings to 3,5-Dichloro-2(1H)-pyrazinones2015In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 5, p. 978-986Article in journal (Refereed)
    Abstract [en]

    The development of a robust palladium-catalysed urea N-arylation protocol to install various ureas at the 3-position of the 2(1H)-pyrazinone scaffold is described. The method involves Pd(OAc)2 in combination with bidentate ligands, xantphos [4,5-bis(diphenylphosphino)-9,9-dimethylxanthene] in particular, and resulted in good to excellent coupling yields of aliphatic, aromatic, and sterically hindered ureas. Furthermore, the C-3 chlorine was shown to be selectively displaced in the presence of aryl halide ureas, and this finding was supported by density functional theory (DFT) calculations. This allows further diversification of the scaffold for the production of compound libraries. Overall, the protocol facilitates further exploitation of pyrazinones as beta-sheet-inducing scaffolds in the development of sophisticated peptidomimetics/protease inhibitors. This is exemplified here by the synthesis of a new pyrazinone-based hepatitis C virus (HCV) NS3 protease inhibitor.

  • 6.
    Belfrage, Anna Karin
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Wakchaure, Prasad
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Sandström, Anja
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Palladium-Catalyzed Carbonylation of Aryl Iodides with Sulfinamides2015In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 32, p. 7069-7074Article in journal (Refereed)
    Abstract [en]

    A facile palladium(0)-catalyzed carbonylative protocol for the generation of new acyl-sulfinamides in moderate to good yields is described. Aliphatic and aromatic sulfinamides were exploited as hitherto unexplored nucleophiles in carbonylation chemistry, with use of CO gas generated ex situ from Mo(CO)6 in a sealed two-chamber system. Both electron-poor and electron-rich (hetero)aryl iodides were employed as electrophiles. The two-chamber system and the use of an inorganic base were essential for efficacious synthesis of acyl-sulfinamide products. Finally, it was demonstrated that a one-pot (or single-vial) synthesis of acyl-sulfinamides was feasible under CO at balloon pressure in the presence of Cs2CO3 as base.

  • 7. Chakka, Sai Kumar
    et al.
    Andersson, Pher G
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Maguire, Glenn E. M.
    Kruger, Hendrik G.
    Govender, Thavendran
    Synthesis and Screening of C-1-Substituted Tetrahydroisoquinoline Derivatives for Asymmetric Transfer Hydrogenation Reactions2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 5, p. 972-980Article in journal (Refereed)
    Abstract [en]

    Tetrahydroisoquinoline (TIQ) derivatives exhibit good biological activity. However, utilization of TIQ compounds in asymmetric catalysis is limited. This paper presents a series of TIQ derivatives in asymmetric transfer hydrogenation (ATH) reactions. Chiral TIQ amino alcohol ligands were synthesized and screened for the ATH reaction of aromatic ketones. The effect of a cis- and trans-phenyl substitution at the C-1 position on the ligand backbone was investigated both experimentally and computationally. The results showed that the trans orientation on the TIQ scaffold yields higher turnover rates with a selectivity of 94% ee obtained at room temperature with an Ru complex. The cis isomer results in a high turnover rate with no selectivity. The trans isomer gave 99% ee at lower temperatures. Furthermore, it was observed that substitution at the C-3-alpha position results in a drop of the enantioselectivity and the reactivity of the catalyst.

  • 8.
    Chinthakindi, Praveen K.
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
    Arvidsson, Per I.
    Univ KwaZulu Natal, Catalysis & Peptide Res Unit, Durban, South Africa;Karolinska Inst, Sci Life Lab, Drug Discovery & Dev Platform, Stockholm, Sweden;Karolinska Inst, Div Translat Med & Chem Biol, Dept Med Biochem & Biophys, Stockholm, Sweden.
    Sulfonyl Fluorides (SFs): More Than Click Reagents?2018In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 27-28, p. 3648-3666Article, review/survey (Refereed)
    Abstract [en]

    Sulfonyl fluoride (SF) containing substances are currently attracting enormous attention among practitioners of both chemical biology and synthetic organic chemistry. The groups of Jones and Liskamp have demonstrated the potential of sulfonyl fluorides as selective covalent inhibitors in studies related to drug discovery and chemical biology, respectively, in the last few years. The Sharpless group has extended the repertoire of click-reactions to those involving sulfonyl fluorides, that is, sulfur-fluoride exchange (SuFEx), a development that quickly triggered the interest in this functional group in the community of synthetic organic chemists. In this microreview, we aim to give an account of the synthetic chemistry surrounding sulfonyl fluoride containing substances from a historical perspective to present day developments.

  • 9.
    Chinthakindi, Praveen K.
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
    Benediktsdottir, Andrea
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
    Ibrahim, Ayah
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
    Wared, Atta
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
    Aurell, Carl-Johan
    AstraZeneca, Large Scale Chem, Early Chem Dev, Pharmaceut Sci,IMED Biotech Unit, S-43183 Gothenburg, Sweden.
    Pettersen, Anna
    AstraZeneca, Early Prod Dev, Pharmaceut Sci, IMED Biotech Unit, S-43183 Gothenburg, Sweden.
    Zamaratski, Edouard
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
    Arvidsson, Per I.
    Karolinska Inst, Sci Life Lab, Drug Discovery & Dev Platform, S-17177 Stockholm, Sweden;Karolinska Inst, Dept Med Biochem & Biophys, Div Translat Med & Chem Biol, S-17177 Stockholm, Sweden;Univ KwaZulu Natal, Catalysis & Peptide Res Unit, ZA-4000 Durban, South Africa.
    Chen, Yantao
    AstraZeneca, Med Chem, Cardiovasc Renal & Metab, IMED Biotech Unit, S-43183 Gothenburg, Sweden.
    Sandström, Anja
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
    Synthesis of Sulfonimidamide-Based Amino Acid Building Blocks with Orthogonal Protecting Groups2019In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 5, p. 1045-1057Article in journal (Refereed)
    Abstract [en]

    Herein, we report the synthesis of novel sulfonimidamides (SIAs) based on amino acid building blocks using a one-pot method from tert-butyldiphenylsilyl-protected (TBDPS) sulfonamides, as well as exploration of orthogonal deprotection strategies. Among the several protecting groups investigated, TBDPS showed higher conversion, allowed UV detection and simple diastereomeric separation; in particular in combination with amino acid tert-butyl esters. Moreover, we applied the present method to synthesize cyclic five-membered acyl sulfonimidamides in two steps. The described synthesis of SIA-based amino acid building blocks in combination with the orthogonal protection groups provide access to unnatural amino acid building blocks useful for further incorporation into larger molecules, such as peptide-based transition-state analogues and peptidomimetics. The chirality of the SIA group, as well as its additional point of diversity provided by the extra NH group, creates opportunities for the development of unique compound libraries that explore new chemical space, which is of considerable importance for the pharmaceutical and agrochemical industry.

  • 10.
    Chow, Shiao Y.
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.
    Odell, Luke R.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.
    Eriksson, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.
    Low-Pressure Radical 11C-Aminocarbonylation of Alkyl Iodides through Thermal Initiation2017In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2017, no 8, p. 1236-1236Article in journal (Refereed)
  • 11.
    Chow, Shiao Y.
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Odell, Luke R.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Eriksson, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Low-Pressure Radical C-11-Aminocarbonylation of Alkyl Iodides through Thermal Initiation2016In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 36, p. 5980-5989Article in journal (Refereed)
    Abstract [en]

    A radical C-11-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into C-11-labelled amides, including the 11-HSD1 inhibitor [carbonyl-C-11]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated C-11-aminocarbonylation, which is limited to the preparation of C-11-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon-[C-11]CO delivery unit represents a simple and convenient alternative to previous radical C-11-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.

  • 12.
    Dahl, Kenneth
    et al.
    Karolinska Institute, Stockholm, Sweden.
    Nordeman, Patrik
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    11C-Acetylation of Amines with [11C]Methyl Iodide with Bis(cyclopentadienyldicarbonyliron) as the CO Source2017In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 38, p. 5785-5788Article in journal (Refereed)
    Abstract [en]

    We describe herein a novel approach for the direct 11C-acetylation of amines. The carbonylative protocol is palladium-mediated, uses bis(cyclopentadienyldicarbonyliron) as the CO source, and [11C]methyl iodide or [11C]methyl iodide-D3 as a radioactive precursor. A set of functionalized primary and secondary amines was 11C-labelled in radiochemical yields ranging from 7–85 %. The potential use of this method for positron emission tomography radiotracer production was additionally demonstrated by the radiosynthesis of [11C]lacosamide, [11C]melatonine, and [11C]acecainide in 44–55 % RCY.

  • 13.
    Dahl, Kenneth
    et al.
    Karolinska Insititute, Ctr Psychiat Res, Karolinska Hosp, Dept Clin Neurosci, SE-17176 Stockholm, Sweden..
    Nordeman, Patrik
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    C-11-Carbonylation through in Situ Generated C-11-Benzoyl Chlorides with Tetrabutylammonium Chloride as Chloride Source2017In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 18, p. 2648-2651Article in journal (Refereed)
    Abstract [en]

    Aromatic C-11-containing acids, amides, esters, and aldehydes were obtained through a novel C-11-carbonylative reaction. In the two-step process, aryl iodides are first reacted with (CO)-C-11 and tetrabutylammonium chloride in a palladium-mediated reaction to yield C-11-benzoyl chlorides in situ. The crude mixture is then further treated with either a hydroxide, amine, alcohol, or a hydride in a second vial to furnish the final C-11-carbonyl product. The monodentate ligand tri-tert-butylphosphonium tetrafluoroborate was proven to be crucial for obtaining high radiochemical yields (RCY). A wide range of C-11-containing carbonyl compounds were successfully radiolabeled in moderate to excellent RCYs, ranging from 41-93%. The synthetic retinoic acid tamibarotene was obtained in a RCY of 89%, whereas the Boc-protected procainamide was labelled in 68% RCY, which is a significantly increase (2-3 fold) in RCY compared to other published methods.

  • 14.
    Eriksson, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Åberg, Ola
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Långström, Bengt
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation2007In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 3, p. 455-461Article in journal (Refereed)
    Abstract [en]

    Two methods are presented for the synthesis of acrylamides labelled with C-11 (beta(+), t(1/2) = 20.4 min) and C-11 in the carbonyl position. In the first method, [1-C-11]acrylic acid is synthesised from [C-11]carbon monoxide by palladium-mediated hydroxy-carbonylation of acetylene. The labelled carboxylic acid is converted into the acyl chloride and subsequently treated with amine to yield N-benzyl[carbonyl(11)C]acrylamide, The second method utilizes [C-11]carbon monoxide in a palladium-mediated carbonylative cross-coupling of vinyl halides and amines. A higher radiochemical yield is achieved with the latter method and the amount of amine needed is decreased to 1/20. The C-11-labelled acrylamides were isolated in up to 81 % decay-corrected radiochemical yield. Starting from 10 +/- 0.5GBq of [C-11]carbon monoxide, N-benzyl[carbonyl-C-11]acrylamide was obtained in 4 min with a specific radioactivity of 330 +/- 4 GBq mu mol-(1). Co-labelling with C-11 and C-13 enabled confirmation of the labelled position by C-13 NMR spectroscopy.

  • 15. Eriksson, Kristofer
    et al.
    Verho, Oscar
    Nyholm, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Inorganic Chemistry.
    Oscarsson, Sven
    Backvall, Jan-E.
    Dispersed Gold Nanoparticles Supported in the Pores of Siliceous Mesocellular Foam: A Catalyst for Cycloisomerization of Alkynoic Acids to gamma-Alkylidene Lactones2015In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 10, p. 2250-2255Article in journal (Refereed)
    Abstract [en]

    A versatile approach for the production of dispersed thiol-stabilized gold nanoparticles in the pores of siliceous mesocellular foam (MCF) is described. The reported method is based on an electrochemical oxidation of a gold surface generating oxidative Au-III species, which give rise to a surface-confined redox reaction yielding MCF-supported Au-I thiolates. By reducing the corresponding Au-I-S-MCF species with sodium borohydride, thiol-stabilized gold nanoparticles in the size range of 1-8 nm were obtained as determined by transmission electron microscopy. Elemental analysis indicated an Au loading of 3% (w/w) on the MCF. The surface-confined Au nanoparticles were used to catalyze the cycloisomerization of alkynoic acids to the corresponding -alkylidene lactones in high efficiency and complete 5-exo-dig selectivity under mild reaction conditions.

  • 16.
    Ghirmai, Senait
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Mume, Eskender
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Henssen, Cecile
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Ghaneolhusseini, Hadi
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Lundqvist, Hans
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Tolmachev, Vladimir
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Sjöberg, Stefan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Orlova, Anna
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Synthesis and Radioiodination of Some 9-Aminoacridine Derivatives2004In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 17, p. 3719-3725Article in journal (Refereed)
  • 17.
    Itsenko, Oleksiy
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Blom, Elisabeth
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Långström, Bengt
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Kihlberg, Tor
    The Use of Lithium Amides in the Palladium-Mediated Synthesis of [Carbonyl-11C]Amides2007In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2007, no 26, p. 4337-4342Article in journal (Refereed)
    Abstract [en]

    Weakly nucleophilic amines were converted into the corresponding lithium amides and used in either one- or two-pot palladium mediated-reactions with [11C]carbon monoxide and aryl iodides. It was found that palladium acyl complexes may be prepared in a separate step and have sufficient lifetime to be used in a subsequent reaction with a nucleophile. This two-pot procedure was used for the labelling synthesis of eleven amides (nine of which are analogues of WAY-100635, a 5-HT1A radioligand) from weakly nucleophilic amines. The results were compared to a direct one-pot procedure using lithium amides. Both approaches extend the scope of palladium-mediated carbonylation using [11C]carbon monoxide and aryl iodides allowing use of weakly nucleophilic amines.

  • 18. Kathiravan, Subban
    et al.
    Nicholls, Ian A.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Rhodium-Catalyzed Oxidative Perfluoroalkenylation by Carbonyl Group Directed C-H Bond Activation2014In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 32, p. 7211-7219Article in journal (Refereed)
    Abstract [en]

    The selective activation of C-H bonds under mild Rh-III catalytic conditions has been developed for the perfluoroalkenylation of various cyclic and acyclic aromatic ketones. This protocol uses versatile reagents and mild conditions. It requires a very low catalyst loading and has exceptional functional group tolerance as well as provides products in good to excellent yields. An application of this approach was described for the preparation of perfluoroethyl acrylate derivatives of biologically active substances.

  • 19.
    Motwani, Hitesh V.
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Diarylated Ethanones from Mo(CO)(6)-Mediated and Microwave-Assisted Palladium-Catalysed Carbonylative Negishi Cross-Couplings2013In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2013, no 22, p. 4729-4733Article in journal (Refereed)
    Abstract [en]

    Two protocols for palladium-catalysed carbonylative Negishi cross-couplings were developed for aryl iodides and aryl bromides. The two main breakthroughs were that molybdenum hexacarbonyl [Mo(CO)(6)] could be used as a solid in situ source of CO, and that controlled microwave irraditaion could be used for heating. Consequently, the reactions were safe (in contrast to when CO gas was used) and fast (in comparison to when conventional heating was used). The carbonylative cross-coupling reactions were carried out using commercially available benzylzinc bromide in closed vials (90-120 degrees C for 0.5-1 h) to give a set of diarylated ethanones, a common pharmacophore found in several pharmaceuticals, in moderate to high isolated yields (47-84%). The mild three-component carbonylation protocol presented here is operationally simple, safe, and rapid, and the formation of the carbonylative Negishi cross-coupling product is favoured over the product of Negishi cross-coupling.

  • 20.
    Nachtigall, Olaf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Lomoth, Reiner
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
    Dahlstrand, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Lundstedt, Anna
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Webb, Matthew J
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Pyrene–Azobenzene Dyads and Their Photochemistry2014In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2014, no 5, p. 966-972Article in journal (Refereed)
    Abstract [en]

    The facile synthesis of three new folding azobenzene-pyrene systems 13, connected together by a serendipitously obtained and unpredicted ester linkage, is reported. Additional characterization of the photochemistry of these systems revealed variations in azobenzene photoisomerization (trans-cis and cis-trans) and quenching of pyrene fluorescence, as a result of intra-excitation energy transfer from the pyrene chromophore to an azobenzene. Through the use of aryl substituent electronic effects to tune the absorption properties of the azobenzene relative to the pyrene, we show that efficient photo-switching can be achieved when the trans-azobenzene absorbance band is well separated from that of the pyrene (compound 1), whereas overlap of the corresponding absorbance bands in the cases of 2 and 3 significantly compromises trans-cis isomerization by enhancing cis-trans interconversion.

  • 21. Naicker, Tricia
    et al.
    Arvidsson, Per I.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Kruger, Hendrik G.
    Maguire, Glenn E. M.
    Govender, Thavendran
    Microwave-Assisted Synthesis of Guanidine Organocatalysts Bearing a Tetrahydroisoquinoline Framework and Their Evaluation in Michael Addition Reactions2012In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 17, p. 3331-3337Article in journal (Refereed)
    Abstract [en]

    The simple and practical syntheses of chiral guanidine organocatalysts and their evaluation in the asymmetric Michael addition reaction of malonates and beta-keto esters with nitro-olefins is reported. These organocatalysts are the first of their kind based on a tetrahydroisoquinoline framework. In addition, a microwave-assisted procedure for introducing the guanidine unit onto amino amide derivatives is reported. The chiral products were obtained with quantitative chemical efficiency (up to 99 % yield) and excellent enantioselectivity (up to 97 % ee).

  • 22. Naicker, Tricia
    et al.
    Arvidsson, Per I
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Kruger, Hendrik G
    Maguire, Glenn E M
    Govender, Thavendran
    Tetrahydroisoquinoline-Based N-Oxides as Chiral Organocatalysts for the Asymmetric Allylation of Aldehydes2011In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2011, no 34, p. 6923-6932Article in journal (Refereed)
    Abstract [en]

    The short synthesis of a series of novel chiral N-oxideorganocatalysts and their evaluation in the asymmetric allylation reaction of aromatic and α-β-unsaturated aldehydes with allyltrichlorosilane is reported. These readily modifiable organocatalysts are the first of their kind based on the tetrahydroisoquinoline framework. The chiral homoallyl products were obtained with good chemical efficiency (up to 93 % yield) and high enantioselectivity (up to 91 % ee) under mild reaction conditions (23 °C).

  • 23.
    Odell, Luke R.
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Lindh, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry. ORGFARM.
    Gustafsson, Tomas
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Continuous Flow Palladium(II): Catalyzed Oxidative Heck Reactions with Arylboronic Acids2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 12, p. 2270-2274Article in journal (Refereed)
    Abstract [en]

    Palladium(II)-catalyzed oxidative Heck reactions were investigated under continuous flow conditions. Selective, fast and convenient protocols for the coupling of arylboronic acids with electron-rich and electron-poor olefins were developed by using a commercially available flow reactor.

  • 24. Parada, Giovanny A.
    et al.
    Glover, Starla D.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
    Orthaber, Andreas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Hammarström, Leif
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
    Ott, Sascha
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Hydrogen Bonded Phenol-Quinolines with Highly Controlled Proton-Transfer Coordinate2016In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 20, p. 3365-3372Article in journal (Refereed)
    Abstract [en]

    A series of polycyclic phenols with intramolecular hydrogen bonds (IMHB) to quinolines was synthesized by Friedlander annulation of cycloalkanone-functionalized anisoles with 2-aminobenzaldehyde. The prepared compounds represent the first series of IMHB phenols in which the substitution and conjugation patterns between the phenols and the hydrogen bond acceptors are kept constant, and in which comparable electronic interaction between the two subunits is thus ensured. The distance and relative orientation between the phenolic OH and the quinolone nitrogen atom is controlled by 1,3-cycloalkadienes of different ring sizes to which the phenol and quinoline subunits are formally annulated. H-1 delta(OH) chemical shift and Xray crystal structure characterization support the conclusion that the size and conformational preference of the 1,3-cycloalkadiene rings control the H-bond geometry and strength. As a result, the oxygen to nitrogen distances differ by as much as 0.30ss the seri.

  • 25.
    Quan, Xu
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Parihar, Vijay Singh
    Bera, Milan
    Andersson, Pher G.
    Iridium Catalysts with Chiral Bicyclic Pyridine-Phosphane Ligands for the Asymmetric Hydrogenation of Olefins2014In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2014, no 1, p. 140-146Article in journal (Refereed)
    Abstract [en]

    New bicyclic pyridine-phosphane ligands were prepared, and their iridium complexes were evaluated in asymmetric hydrogenation of trisubstituted olefins with non-coordinating and weakly coordinating substituents. The iridium catalysts showed high reactivity and enantioselectivity for both types of olefins.

  • 26.
    Rahman, Obaidur
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Llopi, Jordi
    Långström, Bengt
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Organic Bases as Additives to Improve the Radiochemical Yields of [11C]Ketones Prepared by the Suzuki Coupling Reaction2004In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2004, no 12, p. 2674-2678Article in journal (Refereed)
    Abstract [en]

    The Suzuki cross-coupling reaction was employed in the syntheses of eight new [11C-carbonyl]ketones. The reactions between the corresponding boronic acids and the corresponding triflates were performed in the presence of [11C]carbon monoxide and a palladium(0) complex as the catalyst. Lithium bromide was added to facilitate the reactions, and different bases were tested to improve the radiochemical yields. All the ketones were synthesised, with the achievement of isolated radiochemical yields (decay-corrected) of between 14 and 74%. Important improvements in the radiochemical yield were achieved by use of tetrabutylammonium fluoride in the synthesis of ketones incorporating alkyl groups, while potassium tert-butoxide was the best base among those tested for improving the radiochemical yields in the syntheses of biaryl ketones. The optimal amount of base was determined in all cases. Only for compounds 3e and 3h were better radiochemical yields obtained when no base was used. No radiochemical impurities were detected after isolation of the compounds. The specific radioactivity for compound 3a was determined, and a value of 200 GBq/μmol was obtained. Compound 3b was labelled simultaneously with [11C] and (13C)carbon monoxide and the position of the labelled atom was determined and confirmed by 13C NMR spectrometry. Tetrabutylammonium fluoride and potassium tert-butoxide are reported as useful bases for Suzuki carbonylation with [11C]/(13C)carbon monoxide.

  • 27.
    Roslin, Sara
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Odell, Luke R.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Visible-Light Photocatalysis as an Enabling Tool for the Functionalization of Unactivated C(sp(3))-Substrates2017In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2017, no 15, p. 1993-2007Article, review/survey (Refereed)
    Abstract [en]

    Over the past decade, visible-light photocatalysis has emerged as one of the brightest and most dynamic fields in modern organic chemistry. By employing a transition-metal- or organic-dye-based photocatalyst in conjunction with a low-energy visible-light source, this synthetic manifold allows the facile generation of radical intermediates that can subsequently be directed through a wide range of transformations. Although initial studies focused largely on the functionalization of stabilized radical intermediates, over the past few years significant efforts have been directed towards the functionalization of challenging unactivated radical precursors. In this review we summarize the recent developments in the use of visible-light photocatalysis for the functionalization of unactivated C(sp(3))-substrates.

  • 28.
    Sawant, Rajiv T.
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Stevens, Marc Y.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Odell, Luke R.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Rapid Access to Polyfunctionalized 3,4-Dihydroquinazolinones through a Sequential N-Acyliminium Ion Mannich Reaction Cascade2015In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 35, p. 7743-7755Article in journal (Refereed)
    Abstract [en]

    A microwave-promoted one-pot, three-component sequential cyclization-Mannich reaction of unactivated ketones, o-formyl carbamates and primary amines has been developed. Cyclic N-acyliminium ions are generated in situ from the carbamate and amine starting materials. This metal-free cascade protocol provides rapid access to structurally diverse 3,4-dihydroquinazolinones in good to excellent yields with high regioselectivity for the terminal methyl group, in the case of unsymmetrical methyl alkyl ketones. Key features of the developed protocol include its operational simplicity, ease of product purification, and wide functional group tolerance.

  • 29. Sellstedt, Magnus
    et al.
    Nyberg, Anders
    Rosenbaum, Erik
    Engström, Patrik
    Wickström, Malin
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Medical Sciences, Clinical Pharmacology.
    Gullbo, Joachim
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Medical Sciences, Clinical Pharmacology.
    Bergström, Sven
    Johansson, Lennart B. -A.
    Almqvist, Fredrik
    Synthesis and Characterization of a Multi Ring-Fused 2-Pyridone-Based Fluorescent Scaffold2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 32, p. 6171-6178Article in journal (Refereed)
    Abstract [en]

    A series of compounds based on a novel fluorescent scaffold have been synthesized. Most of the compounds displayed high quantum yields of fluorescence and unusually long fluorescence lifetimes. HeLa cells were treated with one of the compounds and its use as a fluorescent dye was demonstrated with fluorescence confocal microscopy.

  • 30.
    Söderström, Marcus
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
    Zamaratski, Edouard
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
    Odell, Luke R.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry.
    Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles Using BF3⦁SMe22019In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 31-32, p. 5402-5408Article in journal (Refereed)
    Abstract [en]

    Herein, a general, solvent-free and straightforward thiomethylation of electron deficient heterocycles using BF3⦁SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3⦁SMe2

    towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non-malodorous reagent while the discovery of novel chemical transformations using BF3⦁SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent.

  • 31. Thorson, Rachel
    et al.
    Woller, Garrett
    Driscoll, Zakarias
    Geiger, Brooke
    Moss, Crystal
    Schlapper, Ashley
    Speetzen, Erin
    Bosch, Eric
    Erdelyi, Mate
    Bowling, Nathan
    Intramolecular Halogen Bonding in Solution: 15N, 13C, and 19F NMR Studies of Temperature and Solvent Effects2015In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 8, p. 1685-1695Article in journal (Refereed)
    Abstract [en]

    A model system for the investigation of intramolecular halogen bonds is introduced. Two molecules capable of intramolecular halogen bonding have been studied in comparison with eight control compounds by 15N, 13C, and 19F NMR spectroscopy. Iodine‐ and bromine‐centered halogen bonds are indicated by decreases in the 15N NMR chemical shifts of the halogen bond acceptor atom of approximately 6 and 1 ppm, respectively. 13C NMR chemical shifts of the alkynyl carbons in 2‐ethynylpyridine systems are good indicators of halogen bonding, with differences of up to 2.4 ppm between halogen‐bonded and related control compounds. Halogen bond strengths in different solvents, as indicated by 19F NMR chemical shifts, decrease in the following order: Cyclohexane > toluene > benzene > dichloromethane > acetone > pyridine. Chemical shift effects associated with the structural and electronic properties of intramolecular halogen‐bonded systems are modeled well by calculations at the B3LYP/6‐311+G(2d,p) level of theory.

  • 32.
    Wakchaure, Prasad
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Borhade, Sanjay
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sandström, Anja
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Arvidsson, Per
    Synthesis of Vinyl- and Aryl–Acyl Sulfonimidamides Through Pd-Catalyzed Carbonylation Using Mo(CO)6 as ex situ CO Source2015In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 1, p. 213-219Article in journal (Refereed)
1 - 32 of 32
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