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Hydrogen-mediated C-C bond formation – Professor Michael Krische

Wednesday, 16 December 2020

4:00 pm

Online event

Hydrogen-mediated C-C bond formation – Professor Michael Krische

We're very fortunate to have Professor Michael Krische to talk to us about carbon bond formation! If it weren't for the pandemic, we wouldn't have been able to hear from him as he's from Texas!

"Stereo- and site-selective methods for the byproduct-free modification of unprotected organic compounds that occur through the addition or redistribution of hydrogen are natural endpoints in the advancement of methods for efficient, green chemical synthesis.(1) Progress toward this goal requires a departure from reactants that embody non-native structural elements, such as premetalated reagents, directing/protecting groups and chiral auxiliaries. Our laboratory has developed a broad, new family of reductive C-C bond formations that merge the characteristics of catalytic hydrogenation and carbonyl addition.(2) Hydrogenation or transfer hydrogenation of π-unsaturated reactants in the presence of C=X (X = O, NR) bonds delivers products of carbonyl or imine addition. In related hydrogen auto-transfer reactions, alcohols served dually as reductants and carbonyl proelectrophiles, enabling direct conversion of lower alcohols to higher alcohols.(3) Such hydrogen-mediated C-C bond formations contribute to a departure from the use of stoichiometric organometallic reagents, and the issues of safety, selectivity, and waste posed by their use.(1-4)"

Professor Michael J. Krische obtained a B.S. degree in Chemistry from the University of California at Berkeley (1989), where he performed research with Professor Henry Rapoport. After a year abroad as a Fulbright Fellow, he initiated doctoral studies at Stanford University with Professor Barry Trost as a Veatch Graduate Fellow. Following receipt of his Ph.D. degree (1996), he joined the laboratory of Nobel Laureate Professor Jean-Marie Lehn at the Université Louis Pasteur as an NIH Post-Doctoral Fellow. In 1999, he joined the faculty at the University of Texas at Austin. Professor Krische was promoted directly to the rank of full professor (2004), skipping the associate rank, and shortly thereafter appointed the Robert A. Welch Chair in Science (2007). Professor Krische has pioneered a broad, new family of byproduct-free catalytic C-C bond formations that merge the characteristics of catalytic hydrogenation and carbonyl addition: (a) Hydrogen-mediated reductive couplings of π-unsaturated feedstocks with carbonyl compounds or imines and (b) related hydrogen auto-transfer reactions for the direct stereo- and site-selective conversion of lower alcohols to higher alcohols.
Professor Krische’s research has been recognized by numerous awards, including the NSF-CAREER Award (2000), Cottrell Scholar Award (2002), Eli Lilly Granteeship for Untenured Faculty (2002), Frasch Award in Chemistry (2002), Dreyfus Teacher-Scholar Award (2003), Sloan Fellowship (2003), Johnson & Johnson Focused Giving Award (2005), Solvias Ligand Prize (2006), Presidential Green Chemistry Award (2007), ACS Corey Award (2007), Dowpharma Prize (2007), Novartis Lectureship (2008), Tetrahedron Young Investigator Award (2009), Humboldt Senior Research Award (2009-2011), Mukaiyama Award (2010), Glaxo-Smith-Kline Scholar Award (2011), ACS Cope Scholar Award (2012), JSPS Fellow (2013), Eun Lee Lectureship Award, Korea (2015), Royal Society of Chemistry, Pedlar Award (2015), AAAS Fellow (2017), Ta-Shue Chou Lectureship Award, Institute of Chemistry, Academia Sinica, Taiwan (2019), ACS Award for Creative Work in Synthetic Organic Chemistry (2020).

(1) “Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis,” Doerksen, R. S.; Meyer, C. C.; Krische, M. J. Angew. Chem. Int. Ed. 2019, 58, 14055.
(2) “Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods,” Hassan, A.; Krische, M. J. Org. Proc. Res. Devel. 2011, 15, 1236.
(3) “Catalytic Enantioselective Carbonyl Allylation and Propargylation via Alcohol Mediated Hydrogen Transfer: Merging the Chemistry of Grignard and Sabatier,” Kim, S. W.; Zhang, W.; Krische, M. J. Acc. Chem. Res. 2017, 50, 2371.
(4) “Metal Catalyzed Reductive Coupling of Olefin-Derived Nucleophiles: Reinventing Carbonyl Addition,” Nguyen, K. D.; Park, B. Y.; Luong, T.; Sato, H.; Garza, V. J.; Krische, M. J. Science 2016, 354, 300 (aah5133).

Non-drinking event.

This event is accessible to all.

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