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Michael J Krische

Department of Chemistry

The Robert A. Welch Chair in Science


Phone: 512-232-5892

Office Location
WEL 5.120A

Postal Address
105 E 24TH ST
AUSTIN, TX 78712

B.S., University of California Berkley (1989)
Fulbright Fellowship, Helsinki University (1990)
Ph.D., Stanford University (1996)
Postdoctoral Studies, Universite' Louis Pasteur (1999)



Transition Metal Catalysis, Natural Product Synthesis, Organometallic And Green Chemistry

Carbon-carbon bond formation lies at the heart of chemical synthesis. The largest volume application of homogenous metal catalyzed C-C coupling is alkene hydroformylation, which may be viewed as the prototypical C-C bond forming hydrogenation. Our laboratory is engaged in the first systematic efforts to develop C-C bond forming hydrogenations beyond hydroformylation - processes wherein two or more reactants are hydrogenated to form a single, more complex product. Using cationic rhodium and iridium catalysts, we have found that diverse π-unsaturated reactants reductively couple to carbonyl compounds and imines under hydrogenation conditions, offering a byproduct-free alternative to stoichiometric organometallics in a range of classical C=X (X = O, NR) addition processes. This concept is extended further via “C-C bond forming transfer hydrogenation”. In such processes, the exchange of hydrogen between alcohols and unsaturated reactants serves to generate aldehyde-organometal pairs that combine to give products of carbonyl addition or hydrohydroxyalkylation. Direct alcohol CH-functionalization in this manner is again byproduct-free, and avoids discrete redox manipulations often required to convert alcohols to aldehydes. Using these merged redox-C-C bond construction events, total syntheses of 6-deoxyerythronolide B, bryostatin 7, cyanolide A and roxaticin, and formal syntheses of rifamycin S and scytophycin C, were accomplished. These syntheses are the most concise routes reported, to date, to any member of these natural products families. More broadly, this body of work evokes question of whether all processes that now rely upon premetallated reagents can be conducted catalytically under hydrogenation or transfer hydrogenation conditions in the absence of stoichiometric organometallics.

Doerksen, R. S.; Meyer, C. C.; Krische, M. J. “Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis,” Angew. Chem. Int. Ed. 58 (2019): In Press.

Bender, M.; Turnbull, B. W. H.; Ambler, B. R.; Krische, M. J. “Ru-Catalyzed Insertion of Adjacent Diol Carbon Atoms into C-C bonds: Entry to Type II Polyketides,” Science 357 (2017): 779.

Nguyen, K. D.; Park, B. Y.; Luong, T.; Sato, H.; Garza, V. J.; Krische, M. J. “Metal Catalyzed Reductive Coupling of Olefin-Derived Nucleophiles: Reinventing Carbonyl Addition,” Science 354 (2016): 300.

Shin, I.; Hong, S.; Krische, M. J. “Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation,” J. Am. Chem. Soc. 138 (2015): 14246.

Ketcham, J. M.; Shin, I.; Montgomery, T. P.; Krische, M. J. “Catalytic Enantioselective C-H Functionalization of Alcohols by Redox-Triggered Carbonyl Addition: Borrowing Hydrogen, Returning Carbon,” Angew. Chem. Int. Ed. 53 (2014): 9142.

Zbieg, J. R.; Yamaguchi, E.; McInturff, E. L.; Krische, M. J. “Enantioselective C-H Crotylation of Primary Alcohols via Hydrohydroxyalkylation of Butadiene,” Science 336 (2012): 324.

  • ACS Award for Creative Work in Synthetic Organic Chemistry, 2020
  • Ta-Shue Chou Lectureship Award, Institute of Chemistry, Academia Sinica, Taiwan, 2019
  • Fellow of the American Association for the Advancement of Science (AAAS), 2017
  • Royal Society of Chemistry, Pedlar Award, 2015
  • Eun Lee Lectureship, Korea, 2015
  • JSPS Fellow, 2013
  • ACS Cope Scholar Award, 2013
  • Fellow of the Royal Society of Chemistry, 2013
  • GlaxoSmithKline Scholar Award, 2011
  • Mukaiyama Award, 2010
  • Humboldt Research Award, 2009
  • Tetrahedron Young Investigator Award, 2009
  • Novartis Lectureship Award, 2008
  • Presidential Green Chemistry Award, 2007
  • Dowpharma Prize, 2007
  • Elias J. Corey Award, 2007
  • Solvias Ligand Prize, 2006
  • Johnson & Johnson Focused Giving Award, 2005
  • Japanese Society of Synthetic Chemistry, Lectureship on Organic Synthesis, 2005
  • Camille Dreyfus Teacher Scholar Award, 2003
  • Alfred P. Sloan Research Fellowship, 2003
  • Cottrell Scholar Award, 2002
  • Lilly Grantee Award, 2002
  • Frasch Foundation Award in Chemistry, 2002
  • National Science Foundation-CAREER Award, 2000
  • NIH Post-Doctoral Fellow, 1997
  • Peter Veatch Fellow, 1995
  • Sigma Xi Fellow, 1990
  • Fulbright Fellow, 1990
  • Presidents Undergraduate Fellow, 1989