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  • 1. Amorati, Riccardo
    et al.
    Pedulli, Gian Franco
    Valgimigli, Luca
    Johansson, Henrik
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Engman, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Organochalcogen Substituents in Phenolic Antioxidants2010In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 12, no 10, p. 2326-2329Article in journal (Refereed)
    Abstract [en]

    Little is known about the ED/EW character of organochalcogen substituents and their contribution to the O-H bond dissociation enthalpy (BDE) in phenolic compounds. A series of ortho- and para-(S,Se,Te)R-substituted phenols were prepared and investigated by EPR, IR, and computational methods. Substituents lowered the O-H BDE by >3 kcal/mol in the para position, while the ortho-effect was modest due to hydrogen bonding ( approximately 3 kcal/mol) to the O-H group.

  • 2.
    Arkhypchuk, Anna I.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    D'Imperio, Nicolas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Ott, Sascha
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    One-Pot Intermolecular Reductive Cross-Coupling of Deactivated Aldehydes to Unsymmetrically 1,2-Disubstituted Alkenes2018In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 20, no 17, p. 5086-5089Article in journal (Refereed)
    Abstract [en]

    The phospha-Peterson reaction between a lithiated secondary phosphane, MesP(Li)TMS, and an aldehyde affords Mes-phosphaalkenes which, upon methanol addition and P-oxidation, react with a second carbonyl compound site specifically to produce unsymmetric alkenes. The E/Z selectivity of the one-pot cross coupling is largely determined by the electronic nature of the aryl substituent of the first aldehyde, with electron-donating groups giving rise to increased amounts of Z-alkenes.

  • 3.
    Arvela, Riina K
    et al.
    University of Connecticut, Department of Chemistry.
    Leadbeater, Nicholas E
    University of Connecticut, Department of Chemistry.
    Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling2005In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 7, no 11, p. 2101-2104Article in journal (Refereed)
    Abstract [en]

    We present here a methodology for the Suzuki coupling of aryl chlorides with phenylboronic acid using Pd/C as a catalyst, water as a solvent, and microwave heating. We show that simultaneous cooling in conjunction with microwave heating prolongs the lifetime of the aryl chloride substrates during the course of the reaction and, as a result, yields of the desired biaryl as well as overall recovery of material can be increased.

  • 4. Aydin, Juhanes
    et al.
    Larsson, Johanna M.
    Selander, Nicklas
    Szabo, Kalman J.
    Pincer Complex-Catalyzed Redox Coupling of Alkenes with Iodonium Salts via Presumed Palladium(IV) Intermediates.2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 13, p. 2852-2854Article in journal (Refereed)
    Abstract [en]

    Palladium pincer complexes directly catalyze the redox coupling reactions of functionalized alkenes and iodonium salts. The catalytic process, which is suitable for mild catalytic functionalization of allylic acetates and electron-rich alkenes, probably occurs through Pd(IV) intermediates. Due to the strong metal-ligand interactions, the oxidn. of phosphine and amine ligands of the pincer complexes can be avoided in the presented reactions. [on SciFinder(R)]

  • 5. Beauseigneur, Alice
    et al.
    Ericsson, Cecilia
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Renaud, Philippe
    Schenk, Kurt
    B-Alkylcatecholborane-Mediated Tandem Radical Conjugated Addition-Aldol Cyclization2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 16, p. 3778-3781Article in journal (Refereed)
    Abstract [en]

    A one-pot procedure involving radical conjugate addition of B-alkylcatecholboranes to enones followed by intramolecular aldol reaction is reported. Application to the stereoselective synthesis of monocyclic and bicyclic products with up to four contiguous stereogenic centers is presented.

  • 6. Bengtson, A
    et al.
    Hallberg, A
    Larhed, M
    Fast synthesis of aryl triflates with controlled microwave heating2002In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 4, no 7, p. 1231-1233Article in journal (Refereed)
    Abstract [en]

    [GRAPHICS] Synthesis of aryl triflates from phenols using N-phenyltriflimide requires only 6 min for completion when conducted with controlled microwave heating. The methodology was applied to both solution- and solid-phase conditions. Ten different aryl triflates were synthesized and isolated in good yields. Applications in high-throughput chemistry are suggested.

  • 7.
    Borhade, Sanjay R.
    et al.
    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 I.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Synthesis of Novel Aryl and Heteroaryl Acyl Sulfonimidamides via Pd-Catalyzed Carbonylation Using a Nongaseous Precursor2013In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 15, no 5, p. 1056-1059Article in journal (Refereed)
    Abstract [en]

    Hitherto unexplored aryl and heteroaryl acyl sulfonimidamides have been prepared through the development of a new Pd-catalyzed carbonylation protocol. This novel methodology, employing sulfonimidamides as nucleophiles and CO gas ex situ released from solid Mo(CO)(6) in a sealed two-chamber system, yields a wide range of carbamate protected acyl sulfonimidamides in good to excellent yields.

  • 8.
    Cadu, Alban
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Watile, Rahul
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Biswas, Srijit
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Orthaber, Andreas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Sjöberg, Per J
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Analytical Chemistry.
    Samec, Joseph
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    One-Pot Synthesis of Keto Thioethers by Palladium/Gold-Catalyzed Click and Pinacol Reactions2014In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 21, p. 5556-5559Article in journal (Refereed)
    Abstract [en]

    An atom-efficient synthesis of keto thioethers was devised via tandem gold/palladium catalysis. The reaction proceeds through a regioselective thiol attack at the β-position of the alcohol, followed by an alkyl, aryl, or benzyl 1,2-shift. Both acyclic and cyclic systems were studied, in the latter case leading to the ring expansion of cyclic substrates.

  • 9.
    Cheruku, Pradeep
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Gohil, Suresh
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Asymmetric Hydrogenation of Enol Phosphinates by Iridium Catalysts Having N, P Ligands2007In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 9, no 9, p. 1659-1661Article in journal (Refereed)
    Abstract [en]

    Enol phosphinates, which are structural analogues of enol acetates, have for the first time been employed as substrates for Ir-catalyzed asymmetric hydrogenation. A number of enol phosphinates have been synthesized and reduced successfully with up to and above 99% ee.

  • 10. Enquist, P A
    et al.
    Nilsson, P
    Larhed, M
    Ultrafast chemistry: Cobalt carbonyl-mediated synthesis of diaryl ketones under microwave irradiation2003In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 5, no 25, p. 4875-4878Article in journal (Refereed)
    Abstract [en]

    [GRAPHICS] By combining the advantages of metal activation, in situ carbon monoxide delivery, and microwave heating, benzophenones were efficiently synthesized in 6-10 s. These ultrafast carbonylation reactions occur under air by flash heating of aryl iodides in the presence of dicobalt octacarbonyl.

  • 11.
    Geng, Xue-Li
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science, Molecular Biomimetics.
    Hu, Qi
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science, Molecular Biomimetics.
    Schäfer, Bernhard
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science, Molecular Biomimetics.
    Ott, Sascha
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science, Molecular Biomimetics.
    Phosphaalkenes in pi-conjugation with Acetylenic Arenes2010In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 12, no 4, p. 692-695Article in journal (Refereed)
    Abstract [en]

    Phosphaalkene inclusion at the periphery of acetylenic arenes results in decreased band gaps of the title compounds as verified by spectroscopic and electrochemical techniques. The electronic coupling between two 1-phosphahex-l-ene-3,5-diyne units is mediated by all paral-substituted arenes and Increases from 4b to 4d.

  • 12. Grigalunas, Michael
    et al.
    Ankner, Tobias
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Norrby, Per-Ola
    Wiest, Olaf
    Helquist, Paul
    Palladium-Catalyzed Alkenylation of Ketone Enolates under Mild Conditions2014In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 15, p. 3970-3973Article in journal (Refereed)
    Abstract [en]

    A protocol for a mild, catalytic, intermolecular alkenylation of ketone enolates has been developed using a Pd/Q-Phos catalyst. Efficient intermolecular coupling of a variety of ketones with alkenyl bromides was achieved with a slight excess of LiHMDS and temperatures down to 0 degrees C.

  • 13.
    Kathiravan, Subban
    et al.
    Linnaeus Univ, Dept Chem & Biomed Sci, Bioorgan & Biophys Chem Lab, SE-39182 Kalmar, Sweden.;Linnaeus Univ, Ctr Biomat Chem, SE-39182 Kalmar, Sweden..
    Nicholls, Ian A.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC. Linnaeus Univ, Dept Chem & Biomed Sci, Bioorgan & Biophys Chem Lab, SE-39182 Kalmar, Sweden.;Linnaeus Univ, Ctr Biomat Chem, SE-39182 Kalmar, Sweden..
    Cobalt Catalyzed, Regioselective C(sp(2))-H Activation of Amides with 1,3-Diynes2017In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 18, p. 4758-4761Article in journal (Refereed)
    Abstract [en]

    The development of a first row transition metal (cobalt)-based catalyst for the as yet unexplored CH activation-driven reaction of 1,3-diynes, themselves a functional class of interest in a range of application areas, to form isoquinolinonesan important structural motif in a number of biologically active substancesis presented. This versatile and inexpensive catalyst employs a covalently attached bidendate-directing group, 8-aminoquinoline. The template directs the CH activation and facilitates the synthesis of a wide range of alkynylated heterocycles under mild conditions and with excellent regioselectivity. This strategy provides a novel and efficient route to diverse heterocyclic frameworks as demonstrated by its late stage application in bisheterocycle syntheses.

  • 14. Kathiravan, Subban
    et al.
    Nicholls, Ian A.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Palladium Catalyzed Vinyltrifluoromethylation of Aryl Halides through Decarboxylative Cross-Coupling with 2-(Trifluoromethyl)acrylic Acid2015In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, no 8, p. 1874-1877Article in journal (Refereed)
    Abstract [en]

    An efficient Pd-catalyzed stereoselective vinyltrifluoromethylation of aryl halides, through decarboxylative cross-coupling with 2-(trifluoromethyl)acrylic acid is described. The ready availability of the starting materials, the high level of functional group tolerance, and excellent E/Z selectivity make this protocol a safe and operationally convenient strategy for efficient synthesis of vinyltrifluoromethyl derivatives.

  • 15.
    Kumar, Sangit
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Johansson, Henrik
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Kanda, Takahiro
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Engman, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Müller, Thomas
    Jonsson, Mats
    Pedulli, Gian Franco
    Petrucci, Silvia
    Valgimigli, Luca
    Catalytic Chain-breaking Pyridinol Antioxidants2008In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 10, no 21, p. 4895-4898Article in journal (Refereed)
    Abstract [en]

    When assayed for their capacity to inhibit azo-initiated peroxidation of linoleic acid in a water/chlorobenzene two-phase system, tellurium-containing 3-pyridinols were readily regenerable by N-acetylcysteine contained in the aqueous phase. The best inhibitors quenched peroxyl radicals more efficiently than alpha-tocopherol, and the duration of inhibition was limited only by the availability of the thiol reducing agent. The compounds were also found to catalyze reduction of hydrogen peroxide in the presence of thiol reducing agent.

  • 16. Larsson, Johanna M.
    et al.
    Zhao, Tony S. N.
    Szabo, Kalman J.
    Palladium-Catalyzed Oxidative Allylic C-H Silylation.2011In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 13, no 7, p. 1888-1891Article in journal (Refereed)
    Abstract [en]

    Pd-catalyzed allylic C-H silylation was performed using hexamethyldisilane as the silyl source. These C-H functionalization reactions occur only in the presence of hypervalent iodine reagents or other strong oxidants and proceed with excellent regioselectivity, providing the linear allylic isomer of the allylsilane products. In demonstrating the first oxidative allylic C-H silylation of alkenes, this study marks an important advance for the catalytic C-H functionalization method. E.g., reaction of CH2:CHCH2CO2CH2Ph with hexamethyldisilane in DME in the presence of 5 mol% Pd(OAc)2 and 2 equiv. of benzoyl peroxide and 4-nitrobenzoic acid as oxidants gave a 77% yield of Me3SiCH2CH:CHCO2CH2Ph. [on SciFinder(R)]

  • 17.
    Larsson, Per-Erik
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Quantum Chemistry.
    Salhi-Benachenhou, Nessima
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Quantum Chemistry.
    Lunell, Sten
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Quantum Chemistry.
    Bicyclo[2.2.1]hepta-2-ene-5-yl-7-ylium Radical Cation: A Theoretical Validation of a Bishomoaromatic Radical Cation Intermediate2003In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 5, no 8, p. 1329-1331Article in journal (Refereed)
    Abstract [en]

    [structure: see text] A natural bond orbital analysis of the distonic bicyclo[2.2.1]hepta-2-ene-5-yl-7-ylium radical cation interprets its structure and radical character by a three-center two-electron bond between C2, C3, and C7 (a bishomoaromatic stabilization) and a singly occupied orbital on C5, n(5). Moreover, B3LYP/6-311+G(d,p) ESR parameters, which agree excellently with experiment, are interpreted in terms of spin polarization in the natural hybrids of sigma(C5-H5), and a dual hyperconjugative effect involving n(5), sigma(C1-H1a), sigma(C1-H1b), and antibonding counterparts.

  • 18. Lehmann, Fredrik
    et al.
    Koolmeister, Tobias
    Odell, Luke R
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Scobie, Martin
    A versatile new synthetic route to 1N-hydroxyindazoles2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 21, p. 5078-5081Article in journal (Refereed)
    Abstract [en]

    A new and versatile cyclization reaction affording rare 1N-hydroxyindazoles is presented. Treatment of 2-nitrobenzylamines with methanolic sodium hydroxide furnishes 1N-hydroxyindazoles regioselectively and in high yield. The reaction tolerates a range of functional groups and electronic effects.

  • 19.
    Norgren, Anna
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Zhang, Suode
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Arvidsson, Per
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Synthesis and circular dichroism spectroscopic investigations of oligomeric β-peptoids with α-chiral side chains2006In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 8, no 20, p. 4533-4536Article in journal (Refereed)
    Abstract [en]

    Biomimetic oligomers are of large interest both as targets for combinatorial and parallel synthetic efforts and as foldamers. For example, shorter peptoid derivatives of beta-peptides, i.e., oligo-N-substituted beta-Ala, have been described as potential lead structures. Herein, we describe a solid-phase synthetic route to beta-peptoids with alpha-chiral aromatic N-substituents up to 11 residues long. Furthermore, the folding propensities of these oligomers were investigated by circular dichroism (CD) spectroscopy.

  • 20.
    Roy, Tamal
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Brandt, Peter
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Wetzel, Alexander
    AstraZeneca, Dept Med Chem Cardiovasc & Metab Dis, Innovat Med & Early Dev Biotech Unit, Pepparedsleden 1, S-43183 Molndal, Sweden..
    Bergman, Joakim
    AstraZeneca, Dept Med Chem Cardiovasc & Metab Dis, Innovat Med & Early Dev Biotech Unit, Pepparedsleden 1, S-43183 Molndal, Sweden..
    Branalt, Jonas
    AstraZeneca, Dept Med Chem Cardiovasc & Metab Dis, Innovat Med & Early Dev Biotech Unit, Pepparedsleden 1, S-43183 Molndal, Sweden..
    Sävmarker, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Larhed, Mats
    Uppsala University, Science for Life Laboratory, SciLifeLab. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Selective Synthesis of Spirooxindoles by an Intramolecular Heck-Mizoroki Reaction2017In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 10, p. 2738-2741Article in journal (Refereed)
    Abstract [en]

    We report a highly diastereoselective synthesis of cydopentene-spirooxindole derivatives via an intramolecular Heck-Mizoroki reaction using aryl bromides as precursors. The reactions were performed under dry conditions or in a DMF-water system. This protocol can be useful to introduce several functionalities to the aromatic nucleus of the spirooxindoles. DFT calculations were performed to rationalize the high antiselectivity. A functionalized spiroproduct was transformed into a cyclic amino acid derivative.

  • 21.
    Rydfjord, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Skillinghaug, Bobo
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Brandt, Peter
    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.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry. Uppsala University, Science for Life Laboratory, SciLifeLab.
    Route to 3-Amidino Indoles via Pd(II)-Catalyzed C-H Bond Activation2017In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 15, p. 4066-4069Article in journal (Refereed)
    Abstract [en]

    We report a facile synthesis of 3-amidino indoles from indoles and cyanamides. The reaction is Pd(II)-catalyzed and proceeds via C-H bond activation of the indole in its 3-position followed by a 1,2-addition of the resulting indole-palladium σ-complex to a cyanamide, which provides the corresponding amidine. The preference for 4,5-diazafluoren-9-one (DAF) as the ligand is investigated using DFT calculations, and a plausible reaction pathway is presented.

  • 22.
    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.
    Sköld, Christian
    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.
    Microwave-Assisted Branching Cascades: A Route to Diverse 3,4-Dihydroquinazolinone-Embedded Polyheterocyclic Scaffolds2016In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 18, no 20, p. 5392-5395Article in journal (Refereed)
    Abstract [en]

    A novel metal-free microwave-assisted branching cascades strategy for the efficient synthesis of 3,4-dihydro-quinazolinone-embedded polyheterocyclic scaffolds is reported. Starting from in situ generated key N-acyliminium ion precursors, 12 distinct and skeletally diverse polycyclic frameworks were accessed in a single step/pot via adjustment of the nucleophile(s) and reaction conditions. Postcascade functionalization of these compounds was also demonstrated, proving the utility of this method in accessing structurally diverse chemical entities.

  • 23.
    Singh, Vijay
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Poon, Jia-fei
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Engman, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Catalytic Antioxidants: Regenerable Tellurium Analogues of Vitamin E2013In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 15, no 24, p. 6274-6277Article in journal (Refereed)
    Abstract [en]

    In an effort to improve the chain-breaking capacity of the natural antioxidants, an octyltelluro group was introduced next to the phenolic moiety in β- and δ-tocopherol. The new vitamin E analogues quenched peroxyl radicals more efficiently than α-tocopherol and were readily regenerable by aqueous N-acetylcysteine in a simple membrane model composed of a stirring chlorobenzene/water two-phase system. The novel tocopherol analogues could also mimic the action of the glutathione peroxidase enzymes.

  • 24.
    Skogh, Anna
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Friis, Stig D.
    Aarhus Univ, Carbon Dioxide Activat Ctr CADIAC, Interdisciplinary Nanosci Ctr iNANO, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark.;Aarhus Univ, Dept Chem, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark..
    Skrydstrup, Troels
    Aarhus Univ, Carbon Dioxide Activat Ctr CADIAC, Interdisciplinary Nanosci Ctr iNANO, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark.;Aarhus Univ, Dept Chem, Gustav Wieds Vej 14, DK-8000 Aarhus C, Denmark..
    Johansson, Anja
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Palladium-Catalyzed Aminocarbonylation in Solid-Phase Peptide Synthesis: A Method for Capping, Cyclization, and Isotope Labeling2017In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 11, p. 2873-2876Article in journal (Refereed)
    Abstract [en]

    A new synthetic approach for introducing N-capping, groups onto peptides attached to a solid support, Combining aminocarbonylation under mild conditions Wing a palladacycle precatalyst and, solid-phase peptide synthesis is reported. The use of la silacarboxylic acid as an in situ CO-releasing molecule allowed the reaction to be performed single vial. The method also enables versatile substitution of side chains, side-chain to side-chain cyclizations, and selective aryl labeling of modified peptides.

  • 25.
    Sävmarker, Jonas
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Rydfjord, Jonas
    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.
    Odell, Luke R.
    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.
    Direct Palladium(II)-Catalyzed Synthesis of Arylamidines from Aryltrifluoroborates2012In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 14, no 9, p. 2394-2397Article in journal (Refereed)
    Abstract [en]

    A fast and convenient synthesis of arylamidines starting from readily available potassium aryltrifluoroborates and cyanamides is reported. The coupling was achieved by Pd(II)-catalysis in a one step 20 min microwave protocol using Pd(O2CCF3), 6-methyl-2,2'-bipyridyl, TFA, and MeOH, providing the corresponding arylamidines in moderate to excellent yields.

  • 26. Teng, Chao
    et al.
    Yang, Xichuan
    Yuan, Chunze
    Li, Chaoyan
    Chen, Ruikui
    Tian, Haining
    Li, Shifeng
    Hagfeldt, Anders
    Sun, Licheng.
    Two Novel Carbazole Dyes for Dye-Sensitized Solar Cells with Open-Circuit Voltages up to 1 V Based on Br-/Br3- Electrolytes.2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 23, p. 5542-5545Article in journal (Refereed)
    Abstract [en]

    Dye-sensitized solar cells (DSCs) based on two novel carbazole dyes and a Br-/Br3- redox mediator in dry CH3CN solns. as electrolytes yielded a Voc of 1.156 V and a η value of 3.68% and a Voc of 0.939 V and a η value of 5.22% under simulated AM 1.5, resp. The dyes have more pos. HOMO levels (1.59 and 1.38 V vs NHE) than the redox potential of Br-/Br3--based electrolytes, which have sufficient driving force to regenerate dyes. Under similar conditions with an I-/I3- instead of a Br-/Br3- redox mediator, DSCs sensitized by the dyes produced a Voc of 0.696 V and a η value of 2.36% and a Voc of 0.621 V and a η value of 4.10%, resp. [on SciFinder(R)]

  • 27.
    Trifonova, Anna
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Diesen, Jarle S.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Chapman, Christopher J.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Application of Phosphine-Oxazoline Ligands in Ir-Catalyzed Asymmetric Hydrogenation of Acyclic Aromatic N-Arylimines2004In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 6, no 21, p. 3825-3827Article in journal (Refereed)
  • 28.
    Tyagi, Mohit
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Poongavanam, Vasanthanathan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Lindhagen, Marika
    AstraZeneca, Early Prod Dev, IMED Biotech Unit, Pharmaceut Sci, Gothenburg, Sweden.
    Pettersen, Anna
    AstraZeneca, Early Prod Dev, IMED Biotech Unit, Pharmaceut Sci, Gothenburg, Sweden.
    Sjö, Peter
    DNDi, 15 Chemin Louis Dunant, CH-1202 Geneva, Switzerland.
    Schiesser, Stefan
    AstraZeneca, Med Chem Resp Inflammat & Autoimmun, IMED Biotech Unit, Gothenburg, Sweden.
    Kihlberg, Jan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.
    Toward the Design of Molecular Chameleons: Flexible Shielding of an Amide Bond Enhances Macrocycle Cell Permeability2018In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 20, no 18, p. 5737-5742Article in journal (Refereed)
    Abstract [en]

    A series of macrocycles inspired by natural products were synthesized to investigate how side-chains may shield amide bonds and influence cell permeability. NMR spectroscopy and X-ray crystallography revealed that the phenyl group of phenylalanine, but not the side-chains of homologous or aliphatic amino acids, shields the adjacent amide bond through an intramolecular NH-pi interaction. This resulted in increased cell permeability, suggesting that NH-pi interactions may be used in the design of molecular chameleons.

  • 29.
    Wetzel, Alexander
    et al.
    AstraZeneca, Dept Med Chem, Innovat Med & Early Dev Biotech Unit, Cardiovasc & Metab Dis, Pepparedsleden 1, SE-43183 Molndal, Sweden.
    Bergman, Joakim
    AstraZeneca, Dept Med Chem, Innovat Med & Early Dev Biotech Unit, Cardiovasc & Metab Dis, Pepparedsleden 1, SE-43183 Molndal, Sweden.
    Brandt, Peter
    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. Uppsala University, Science for Life Laboratory, SciLifeLab.
    Brånalt, Jonas
    AstraZeneca, Dept Med Chem, Innovat Med & Early Dev Biotech Unit, Cardiovasc & Metab Dis, Pepparedsleden 1, SE-43183 Molndal, Sweden.
    Regio- and Stereoselective Synthesis of Functionalized Cyclopentene Derivatives via Mizoroki-Heck Reactions.2017In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 19, no 7, p. 1602-1605Article in journal (Refereed)
    Abstract [en]

    Pd(0)-catalyzed Mizoroki-Heck alkenylations and arylations of protected aminocyclopentenes, prepared in a few steps from Vince lactam, afforded functionalized cyclopentenes in high yields and stereoselectivities. DFT calculations were performed to rationalize the high diastereoselectivities. Functionalized cyclopentene products were transformed into valuable chiral building blocks, such as cyclic γ-amino acids and carbocyclic nucleoside precursors.

  • 30.
    Yan, Jiajie
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Poon, Jia-fei
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Singh, Vijay P
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Gates, Paul
    Engman, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Regenerable thiophenolic radical-trapping antioxidants2015In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, no 24, p. 6162-6165Article in journal (Refereed)
    Abstract [en]

    Diphenyl disulfides carrying alkyltelluro groups in the o-, m-, and p-positions were prepared using ortho-lithiation and lithium halogen exchange reactions. The novel antioxidants showed only minimal inhibitory effect on the azo-initiated peroxidation of linoleic acid in chlorobenzene until reduced to the corresponding thiophenols by tris(2-carboxyethyl)phosphine (TCEP). The best in situ generated thiophenol (from 7c) under these conditions quenched peroxyl radicals more efficiently than α-tocopherol with an almost 3-fold increase in inhibition time.

1 - 30 of 30
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