The PGA Research Group

Suttichat Kerdphon

Part of my research is focused on hydrogen transfer reactions using N-heterocyclic carbene-phosphine iridium catalysts (NHC,P-Ir) and asymmetric hydrogenation using N,P iridium catalysts.  The first part is the use of achiral N-heterocyclic carbene-phosphine iridium complexes catalyzing the methylation of ketones and alkylation of amides using alcohols as the electrophile.  The NHC,P-Ir catalysts that have been developed in our group were employed as catalysts for the methylation of ketones.  The reaction could be carried out under mild condition with low catalyst loading (only 1.0 mol%) to furnish the desired methylated products in up to 98% isolated yield.  In addition, this NHC,P-Ir catalyst was also found to catalyze the N-alkylation of amides with alcohols.  With optimized conditions, the best catalyst could be used with a wide range of substrates at low catalyst loading (only 0.5 mol%) to afford the desired products up to 98% isolated yield.  Second part of my research is the preparation of chiral NHC,P-Ir catalyst for asymmetric hydrogenation of ketones.  These complexes successfully catalyzed the asymmetric hydrogenation of ketones at room temperature under base free conditions to obtain the chiral alcohol products with in high enantiomeric excess (up to 96% ee) in 30 minutes.  The mechanistic details of this catalysts reaction pathway are still under investigation.

Methylation of ketones
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N-alkylation of amides
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Hydrogenation of ketoneskim3

Hydrogenation of Cycloalkenes
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Hydrogenation of Tetrasubstituted olefins

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Publications

[1] An Enantioselective Approach to the Preparation of Chiral Sul- fones by Ir-Catalyzed Asymmetric Hydrogenation.
Byron K. Peters, Taigang Zhou, Janjira Rujirawanich, Alban Cadu, Thishana Singh, Wangchuk Rabten, Sutthichat Kerdphon, and Pher G. Andersson* J. Am. Chem. Soc., 2014, 136, 16557-1656
[2] C-C Coupling of Ketone with Methanol Catalyzed by N- Heterocyclic Carbene-Phosphine Iridium Complex.
Xu Quan, Sutthichat Kerdphon and Pher G. Andersson* Chem. Eur. J., 2015, 21, 3576-3579.
[3] C-N Coupling of Amides with Alcohols Catalyzed by N- Heterocyclic Carbene-Phosphine Iridium complex.
Sutthichat Kerdphon, Xu Quan, Vijay Singh Parihar and Pher G. Andersson* J. Org. Chem., 2015, 80, 11529-11537.
[4] Enantio- and Regioselective Ir-Catalyzed Hydrogenation of Di- and Trisubstituted Cycloalkenes.
Byron K. Peters,† Jianguo Liu,† Cristiana Margarita,† Wangchuk Rabten,† Sutthichat Kerdphon,† Alexander Orebom, Thomas Morsch, and Pher G. Andersson* J. Am. Chem. Soc., 2016, 138, 11930-11935.
†Authors contributed equally to this work.
[5] Revisiting the Stereodetermining Step in Enantioselective Iridi- um-Catalyzed Imine Hydogenation.
Brandon Tutkowski, Sutthichat Kerdphon, Elaine Lime, Paul Hel- quist, Pher G. Andersson* Olaf Wiest* and Per-Ola Norrby* ACS Catal., 2018, 8, 651-632.