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  • 1. Betterley, Nolan M.
    et al.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chaturonrutsamee, Suppisak
    Kongsriprapan, Sopanat
    Surawatanawong, Panida
    Soorukram, Darunee
    Pohmakotr, Manat
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Reutrakul, Vichai
    Kuhakarn, Chutima
    Bi(OTf)(3) Enabled C-F Bond Cleavage in HFIP: Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl)methane2018In: Asian Journal of Organic Chemistry, ISSN 2193-5807, Vol. 7, no 8, p. 1642-1647Article in journal (Refereed)
    Abstract [en]

    Bismuth(III) trifluoromethanesulfonate [Bi(OTf)(3)] mediated mild electrophilic aromatic formylation utilizing difluoro(phenylsulfanyl)methane (PhSCF2H) as a formylating agent in hexafluoro-2-propanol (HFIP) as a recyclable ionizing solvent has been developed. The active formylating species was generated via C-F bond cleavage and was characterized to be a bis(phenylsulfanyl)methyl cation by experimental and computational H-1 and C-13 NMR.

  • 2.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    NHC,P- and N,P-Iridium Catalysts for Hydrogenations and Hydrogen Transfer Reactions2018Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The work described in this thesis is focused on hydrogenation and hydrogen transfer reactions using iridium catalysts. The first part concerns the use of N-heterocyclic carbene-phosphine iridium complexes in alkylation reactions (Chapters 2 and 3) and the hydrogenation of ketones (Chapter 4). A number of N-heterocyclic carbene-phosphine iridium complexes have been prepared and evaluated as catalysts for C-N bond formation of amides using alcohols as the electrophile. This catalytic system can be used with a wide range of substrates at low catalyst loading (only 0.5 mol%) to furnish the desired products in up to 98% isolated yield. The achiral N-heterocyclic carbene-phosphine iridium complexes were also found to catalyze the methylation of ketones with methanol under mild conditions to afford the mono-methylated products in up to 98% isolated yield with low catalyst loading (1.0 mol%). Additionally, several chiral N-heterocyclic carbene-phosphine iridium complexes were synthesized and evaluated in asymmetric hydrogenation of ketones. The reactions were carried out at room temperature under base-free conditions to obtain the chiral alcohols in up to 96% ee in 30 minutes.

    The second part of this thesis (Chapter 5) details the preparation of new N,P-iridium complexes which were found to be highly efficient catalysts for the asymmetric hydrogenation of challenging tetrasubstituted olefins. This catalytic system results in optically active compounds of high enantiomeric excess (up to 98% ee) as the single diasteroisomer.

  • 3.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    N-Heterocyclic Carbene-Phosphine Iridium Catalyzed Alkylation Reactions and Asymmetric Hydrogenation of Ketones2015Licentiate thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis is focused on hydrogen transfer reactions using N-heterocyclic carbenephosphine iridium catalysts and is divided in two parts. The first part describes the use of achiral N-heterocyclic carbene-phosphine iridium complexes catalyzing the methylation of ketones and alkylation of amides using alcohols as the electrophile. In Chapter 2, the N-heterocyclic carbene-phosphine iridium complexes that have been developed in the Andersson group was employed as catalysts for the methylation of ketones. These reactions were found to take place under mild conditions with low catalyst loading (1.0 mol%) to furnish the desired methylated products in up to 98% isolated yield. The achiral N-heterocyclic carbene-phosphine iridium complexes were also found to catalyze the N-alkylation of amides with alcohols, as presented in Chapter 3. It was discovered that the reactivity of the catalysts was highly dependent on the structure of the catalyst. At optimum reaction conditions, the best catalyst could be used with a wide range of substrates at low catalyst loading (0.5 mol%) to afford the desired product up to 98% isolated yield.

    The second part of this thesis details the preparation of chiral N-heterocyclic carbenephosphine iridium complexes and their use in the asymmetric hydrogenation of ketones (Chapter 4). These catalysts were successfully used in the asymmetric hydrogenation of ketones at room temperature under base-free conditions and led to full conversion of chiral alcohol products in 30 min with high enantiomeric excess (up to 96%).

  • 4.
    Kerdphon, Sutthichat
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ponra, Sudipta
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Jianping
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wu, Haibo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iridium-Catalyzed Enantio- and Diastereoselective Hydrogenation of Acyclic Tetra-Substituted OlefinsManuscript (preprint) (Other academic)
  • 5.
    Kerdphon, Sutthichat
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Xu, Quan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Parihar, Vijay Singh
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    C-N Coupling of Amides with Alcohols Catalyzed by N-Heterocyclic Carbene-Phosphine Iridium Complexes2015In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 80, no 22, p. 11529-11537Article in journal (Refereed)
    Abstract [en]

    N-heterocyclic carbene-phosphine iridium complexes (NHC-Ir) were developed/found to be a highly reactive catalyst for N-monoalkylation of amides with alcohols via hydrogen transfer. The reaction produced the desired product in high isolated yields using a wide range of substrates with low catalyst loading and short reaction times.

  • 6.
    Peters, Byron K.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Jianguo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Margarita, Cristiana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rabten, Wangchuk
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Orebom, Alexander
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Morsch, Thomas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantio- and Regioselective Ir-Catalyzed Hydrogenation of Di- and Trisubstituted Cycloalkenes2016In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 36, p. 11930-11935Article in journal (Refereed)
    Abstract [en]

    A number of cyclic olefins Were prepared and evaluated for the asymmetric hydrogenation reaction using novel N,P-ligated iridium imidazote-based Catalysts (Crabtree type). The diversity of these cyclic olefins spanned those having little functionality to others bearing strongly coordinating substituents and heterocycles. Excellent enantioselectivities were observed both for substrates having little functionality (up to >99% ee) and for substrates possessing functional groups several carbons away from the olefin. Substrates having functionalities such as carboxyl groups, alcohols, or heterocycles in the vicinity of the C=C bond were hydrogenated in high enantiomeric excess (up to >99% ee). The hydrogenation was also found to be regioselective, and by controlling the reaction conditions, selective hydrogenation of one of two trisubstituted olefins can be achieved: Furthermore, trisubstituted olefins can be selectively hydrogenated in the presence of tetrasubstituted olefins.

  • 7.
    Peters, Byron K.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Jianguo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Margarita, Cristiana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rabten, Wangchuk
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Paptchikhine, Alexander
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantio- and Regioselective Hydrogenation of Minimally and Densely Decorated Unsaturated CarbocyclesManuscript (preprint) (Other academic)
    Abstract [en]

    Several cyclic prochiral olefins were successfully hydrogenated (>99 conv.,up to >99 % ee) using N,P-ligated iridium catalysts. Minimally functionalisedsubstrates (Class 1) were hydrogenated rapidly and in high ee, whichwas consistent with earlier reports. Substrates having functional groups(Class 2) and heterocycles (Class 3) attached to the unsaturated cycle, were43hydrogenated gradually over a period of time, however, high enantioselectivitywas still maintained (up to >99 % ee). This methodology is a highly practical,general and selective means of preparing chiral cyclohexanes.

  • 8.
    Peters, Byron K.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhou, Taigang
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rujirawanich, Janjira
    Cadu, Alban
    Singh, Thishana
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Uppsala University, Sweden.
    Rabten, Wangchuk
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    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.
    Ponra, Sudipta
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rabten, Wangchuk
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yang, Jianping
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wu, Haibo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Diastereo- and Enantioselective Synthesis of Fluorine Motifs with Two Contiguous Stereogenic Centers2018In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 42, p. 13878-13883Article in journal (Refereed)
    Abstract [en]

    The synthesis of chiral fluorine containing motifs, in particular, chiral fluorine molecules with two contiguous stereogenic centers, has attracted much interest in research due to the limited number of methods available for their preparation. Herein, we report an atom-economical and highly stereoselective synthesis of chiral fluorine molecules with two contiguous stereogenic centers via azabicyclo iridium-oxazoline-phosphine-catalyzed hydrogenation of readily available vinyl fluorides. Various aromatic, aliphatic, and heterocyclic systems with a variety of functional groups were found to be compatible with the reaction and provide the highly desirable product as single diastereomers with excellent enantioselectivities.

  • 10.
    Rabten, Wangchuk
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ponra, Sudipta
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wu, Haibo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    N,P-Iridium Catalyzed Asymmetric Hydrogenation of Vinyl FluoridesManuscript (preprint) (Other academic)
  • 11. Tutkowski, Brandon
    et al.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Limé, Elaine
    Helquist, Paul
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wiest, Olaf
    Norrby, Per-Ola
    Revisiting the Stereodetermining Step in Enantioselective Iridium-Catalyzed Imine Hydrogenation2018In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 8, no 1, p. 615-623Article in journal (Refereed)
    Abstract [en]

    The mechanism for the iridium-catalyzed asymmetric hydrogenation of prochiral imines has been investigated for an experimentally relevant ligand substrate combination using DFT calculations. The possible stereoisomers of the stereodetermining hydride transfer transition state were considered for four possible hydrogenation mechanisms starting from the recently disclosed active catalyst consisting of iridium phosphine-oxazoline with cyclometalated imine substrate. The hydrogenation was found to proceed via an outer sphere pathway. The transition state accurately describes the experimental observations of the active catalyst and provides a structural rationale for the high stereoinduction despite the lack of direct interaction points in the outer-sphere mechanism. The predicted enantioselectivity was consistent with experimental observations. Experimental studies support the hypothesis that the iridacycle forms spontaneously and functions as the active catalyst in the hydrogenation.

  • 12.
    Xu, Quan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    C-C Coupling of Ketones with Methanol Catalyzed by a N-Heterocyclic Carbene-Phosphine Iridium Complex2015In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 21, p. 3576-3579Article in journal (Refereed)
    Abstract [en]

    An N-heterocyclic carbene–phosphine iridium complex system was found to be a very efficient catalyst for the methylation of ketone via a hydrogen transfer reaction. Mild conditions together with low catalyst loading (1 mol %) were used for a tandem process which involves the dehydrogenation of methanol, CC bond formation with a ketone, and hydrogenation of the new generated double bond by iridium hydride to give the alkylated product. Using this iridium catalyst system, a number of branched ketones were synthesized with good to excellent conversions and yields.

  • 13.
    Xu, Quan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rujirawanich, Janjira
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Krajangsri, Suppachai
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Andersson, Pher
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly Active Cationic NHC, Phosphine Iridium Catalysts for Base Free Asymmetric Hydrogenation of KetonesManuscript (preprint) (Other academic)
1 - 13 of 13
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