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  • 1.
    Cadu, Alban
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Iridium Catalysed Asymmetric Hydrogenation of Pyridines2013Licentiate thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis presents the hydrogenation of substituted pyridines using N,P-ligated iridium catalystsin homogeneous media. These iridium catalysts were developed within this research group in thepast decade. This method of hydrogenation is highly stereoselective, and in several cases good to excellent ees were obtained.The hydrogenation of substituted pyridines was studied: by screening for the catalyst giving thehighest conversion and ee, by optimising the reaction conditions and by attempting to improve existingcatalysts. New substrates were synthesised for this process, in particular alkyl substituted Nprotectedpyridines. Their reduction provided chiral piperidines, which could be used as chiralbuilding blocks once deprotected.

    List of papers
    1. Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
    Open this publication in new window or tab >>Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
    2013 (English)In: Asian Journal of Organic Chemistry, ISSN 2193-5807, Vol. 2, no 12, p. 1061-1065Article in journal (Refereed) Published
    Abstract [en]

    Asymmetric hydrogenation of ortho-substituted pyridines catalyzed by N,P-ligated iridium is demonstrated. To facilitate this reaction, the aromaticity of the pyridines was weakened by forming N-iminopyridium ylides. The reactions give very high conversions, and after a single recrystallization, excellent ee of up to 98 % was obtained. This method lends itself to the synthesis of chiral piperidine building blocks.

    Keywords
    hydrogenation, iridium, N-iminopyridium ylides, pyridines, selective catalysis
    National Category
    Organic Chemistry Inorganic Chemistry
    Research subject
    Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-212412 (URN)10.1002/ajoc.201300160 (DOI)000328218000008 ()
    Available from: 2013-12-10 Created: 2013-12-10 Last updated: 2017-01-25Bibliographically approved
  • 2.
    Cadu, Alban
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Noble Metal Catalysed Reductions and Rearrangements2016Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The focus of this thesis has been organometallic catalysis applied to compounds containing heteroatoms which are usually poisonous to metal catalysts, by channelling their innate reactivity advantageously. The studies described in this thesis concentrate, in the first part, on iridium catalysed asymmetric hydrogenation (papers I and II) and in the second part, on gold catalysed internal rearrangements (papers III and IV). In each case, two classes of compounds are studied: pyridinium salts or sulphurous compounds. The asymmetric hydrogenation of pyridinium compounds was performed with 2% loading of N,P-ligated Ir catalyst with I2 additive (paper I) to achieve moderate to good enantiomeric excess (up to 98%). In paper II, olefinic sulphones were hydrogenated with an efficient 0.5% catalytic loading. In most cases full conversion was obtained and with good to excellent ees (up to 99%). The products of these reductions are chiral compounds, which could constitute further chemical building blocks. Palladium and gold were used sequentially in paper III, in order to perform a “Click” thiol-yne reaction followed by a semi-Pinacol rearrangement, leading to isolated yields of up to 98%. In paper IV The gold catalysed rearrangement of alkyl-pyridinium diynes was conducted, with a number of substrates providing >90% NMR yield. A highly selective hydrogenation was performed with a heterogeneous palladium catalyst to yield single diastereomer products. This methodology consists of up to three steps, with two catalysts in one pot.

    List of papers
    1. Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
    Open this publication in new window or tab >>Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines
    2013 (English)In: Asian Journal of Organic Chemistry, ISSN 2193-5807, Vol. 2, no 12, p. 1061-1065Article in journal (Refereed) Published
    Abstract [en]

    Asymmetric hydrogenation of ortho-substituted pyridines catalyzed by N,P-ligated iridium is demonstrated. To facilitate this reaction, the aromaticity of the pyridines was weakened by forming N-iminopyridium ylides. The reactions give very high conversions, and after a single recrystallization, excellent ee of up to 98 % was obtained. This method lends itself to the synthesis of chiral piperidine building blocks.

    Keywords
    hydrogenation, iridium, N-iminopyridium ylides, pyridines, selective catalysis
    National Category
    Organic Chemistry Inorganic Chemistry
    Research subject
    Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-212412 (URN)10.1002/ajoc.201300160 (DOI)000328218000008 ()
    Available from: 2013-12-10 Created: 2013-12-10 Last updated: 2017-01-25Bibliographically approved
    2. An Enantioselective Approach to the Preparation of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation
    Open this publication in new window or tab >>An Enantioselective Approach to the Preparation of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation
    Show others...
    2014 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 136, no 47, p. 16557-16562Article in journal (Refereed) Published
    Abstract [en]

    Several chiral sulfonyl compounds were prepared using the iridium catalyzed asymmetric hydrogenation reaction. Vinylic, allylic and homoallylic sulfone substitutions were investigated, and high enantioselectivity is maintained regardless of the location of the olefin with respect to the sulfone. Impressive stereoselectivity was obtained for dialkyl substitutions, which typically are challenging substrates in the hydrogenation. As expected, the more bulky Z-substrates were hydrogenated slower than the corresponding E isomers, and in slightly lower enantioselectivity.

    Place, publisher, year, edition, pages
    American Chemical Society (ACS), 2014
    National Category
    Organic Chemistry
    Research subject
    Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-236862 (URN)10.1021/ja5079877 (DOI)000345720500016 ()25300238 (PubMedID)
    Available from: 2014-11-24 Created: 2014-11-24 Last updated: 2017-12-05Bibliographically approved
    3. One-Pot Synthesis of Keto Thioethers by Palladium/Gold-Catalyzed Click and Pinacol Reactions
    Open this publication in new window or tab >>One-Pot Synthesis of Keto Thioethers by Palladium/Gold-Catalyzed Click and Pinacol Reactions
    Show others...
    2014 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 16, no 21, p. 5556-5559Article in journal (Refereed) Published
    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.

    Place, publisher, year, edition, pages
    American Chemical Society (ACS), 2014
    Keywords
    Gold, Palladium, thioether, catalysis, synthesis
    National Category
    Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-236857 (URN)10.1021/ol502553p (DOI)000344635200013 ()25325145 (PubMedID)
    Available from: 2014-11-24 Created: 2014-11-24 Last updated: 2017-12-05Bibliographically approved
    4. Dual Gold (I) Catalysed Cyclisation of Dialkynyl Pyridinium salts
    Open this publication in new window or tab >>Dual Gold (I) Catalysed Cyclisation of Dialkynyl Pyridinium salts
    Show others...
    (English)Manuscript (preprint) (Other academic)
    Abstract [en]

    Novel dialkynyl pyridines were synthesised and protected as alkyl salts for dual gold (I) catalysed cycloisomerisation. Different alkyl groups and counter ions were screened for the salts, with benzyl and PF6- providing the best results. The cyclisation led to NMR yields of >95% being obtained for a number of substrates. Step-wise hydrogenation of products could be carried out in one-pot by Pd/C, with selective reduction of the double bonds, followed by deprotection of the Bn group.

    Keywords
    chemistry
    National Category
    Organic Chemistry
    Research subject
    Chemistry with specialization in Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-272369 (URN)
    Available from: 2016-01-13 Created: 2016-01-13 Last updated: 2016-02-12Bibliographically approved
  • 3.
    Cadu, Alban
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Development of iridium-catalyzed asymmetric hydrogenation: New catalysts, new substrate scope2012In: Journal of Organometallic Chemistry, ISSN 0022-328X, E-ISSN 1872-8561, Vol. 714, p. 3-11Article, review/survey (Refereed)
    Abstract [en]

    A review. The asym. hydrogenation of olefins is a tremendously powerful tool used to synthesize chiral mols. The field was pioneered using rhodium- and ruthenium- based catalysts; however, catalysts based on both of these metals suffer from limitations, such as the need for directing substituents near or even adjacent to the olefin. Iridium-based catalysts do not suffer from this flaw and can thus hydrogenate a wide variety of olefins, including some tetra substituted ones. It is also possible for iridium-based catalysts to hydrogenate hetero-π bonds such as those found in heteroarom. rings. This review summarizes the contributions made to this field by the authors in the past few years. [on SciFinder(R)]

  • 4.
    Cadu, Alban
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Andersson, Pher G
    Iridium catalysis: Application of asymmetric reductive hydrogenation2013In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 42, no 40, p. 14345-14356Article in journal (Refereed)
    Abstract [en]

    Iridium, despite being one of the least abundant transition metals, has found several uses. N,P-ligated iridium catalysts are used to perform many highly selective reactions. These methodologies have been developed extensively over the past 15 years. More recently, the application of iridium N,P catalysts in asymmetric hydrogenation has been a focus of research to find novel applications and to expand on their current synthetic utility. The aim of this perspective is to highlight the advances made by the Andersson group.

  • 5.
    Cadu, Alban
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Paptchikhine, Alexander
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Birch Reaction Followed by Asymmetric Iridium-Catalysed Hydrogenation2011In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 23, p. 3796-3800Article in journal (Refereed)
    Abstract [en]

    Birch reaction products are asymmetrically hydrogenated with high enantio- and diastereoselectivity via iridium catalysts. This new method of producing chiral compounds was explored for a variety of 1,3-di- and 1,2,4-tri-substituted cyclohexadienes.

  • 6.
    Cadu, Alban
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Upadhyay, Puspesh K.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Andersson, Pher G.
    Stockholm University.
    Iridium-Catalyzed Asymmetric Hydrogenation of Substituted Pyridines2013In: Asian Journal of Organic Chemistry, ISSN 2193-5807, Vol. 2, no 12, p. 1061-1065Article in journal (Refereed)
    Abstract [en]

    Asymmetric hydrogenation of ortho-substituted pyridines catalyzed by N,P-ligated iridium is demonstrated. To facilitate this reaction, the aromaticity of the pyridines was weakened by forming N-iminopyridium ylides. The reactions give very high conversions, and after a single recrystallization, excellent ee of up to 98 % was obtained. This method lends itself to the synthesis of chiral piperidine building blocks.

  • 7.
    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.

  • 8. Peters, Byron K.
    et al.
    Zhou, Taigang
    Rujirawanich, Janjira
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Cadu, Alban
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Singh, Thishana
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Rabten, Wangchuk
    Kerdphon, Suttichat
    Andersson, Pher G.
    An Enantioselective Approach to the Preparation of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation2014In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 136, no 47, p. 16557-16562Article in journal (Refereed)
    Abstract [en]

    Several chiral sulfonyl compounds were prepared using the iridium catalyzed asymmetric hydrogenation reaction. Vinylic, allylic and homoallylic sulfone substitutions were investigated, and high enantioselectivity is maintained regardless of the location of the olefin with respect to the sulfone. Impressive stereoselectivity was obtained for dialkyl substitutions, which typically are challenging substrates in the hydrogenation. As expected, the more bulky Z-substrates were hydrogenated slower than the corresponding E isomers, and in slightly lower enantioselectivity.

  • 9.
    Tsupova, Svetlana
    et al.
    Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany..
    Cadu, Alban
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry. Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany..
    Stuck, Fabian
    Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany..
    Rominger, Frank
    Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany..
    Rudolph, Matthias
    Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany..
    Samec, Joseph S. M.
    Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden..
    Hashmi, A. Stephen K.
    Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany.;King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia..
    Dual Gold(I)-catalyzed Cyclization of Dialkynyl Pyridinium Salts2017In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 9, no 11, p. 1915-1920Article in journal (Refereed)
    Abstract [en]

    Novel dialkynyl pyridines were synthesized and protected as alkyl salts for dual gold(I)-catalyzed cycloisomerization. Different alkyl groups and counter ions were screened for the salts, with benzyl and hexafluorophosphate providing the best results. The cyclization led to NMR yields of >95% being obtained for a number of substrates. Step-wise hydrogenation of products could be performed in one-pot by Pd/C, with selective reduction of the double bonds, followed by deprotection of the benzyl group.

  • 10.
    Tšupova, Svetlana
    et al.
    Ruprecht-Karls-Universität Heidelberg.
    Cadu, Alban
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Stuck, Fabian
    Ruprecht-Karls-Universität Heidelberg.
    Rominger, Frank
    Ruprecht-Karls-Universität Heidelberg.
    Rudolph, Matthias
    Ruprecht-Karls-Universität Heidelberg.
    Samec, Joseph
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry. Stockholm University.
    Hashmi, A. Stephen K.
    Ruprecht-Karls-Universität Heidelberg.
    Dual Gold (I) Catalysed Cyclisation of Dialkynyl Pyridinium saltsManuscript (preprint) (Other academic)
    Abstract [en]

    Novel dialkynyl pyridines were synthesised and protected as alkyl salts for dual gold (I) catalysed cycloisomerisation. Different alkyl groups and counter ions were screened for the salts, with benzyl and PF6- providing the best results. The cyclisation led to NMR yields of >95% being obtained for a number of substrates. Step-wise hydrogenation of products could be carried out in one-pot by Pd/C, with selective reduction of the double bonds, followed by deprotection of the Bn group.

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