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Department of Chemistry & Biochemistry
The University of Texas at Austin
1 University Station A5300
Austin, TX 78712-0165
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Contact Information
Office: WEL: 5.146
Phone: 232-5892
Lab
Office:
Phone:
Fax: 471-8696
Michael J. Krische
mkrische@mail.utexas.edu
Professor, Faculty
Environmental Science Institute
Director, Center for Green Chemistry and Catalysis
Robert A. Welch Chair in Science
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Research GroupThe Krische Group |
EducationFulbright Fellowship, Helsinki University, 1990 BS, University of California at Berkeley, 1989 PhD, Stanford University, 1996 Postdoctoral Studies, Universite' Louis Pasteur 1999 |
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Affiliations
Center for Nano- and Molecular Science and Technology; Texas Materials Institute; Environmental Science Institute;
Natural Product Synthesis, Catalytic Reaction Development, Organometallic Chemistry and Self-Assembly
Research in the Krische group focuses on catalytic reaction development with attendant applications in natural product synthesis. A central theme involves the identification of new reactivity patterns, the evolution of related catalytic processes and, ultimately, the development of new synthetic strategies. Specific areas of research include: (a) hydrogen-mediated C-C bond formation, (b) nucleophilic catalysis via phosphine conjugate addition, (c) catalytic tandem conjugate addition-electrophilic trapping, and (d) metal-catalyzed [2+2]cycloaddition.
H2-Mediated C-C Bond Formation: Alkene hydroformylation is the largest volume application of homogeneous metal catalysis and the prototypical example of hydrogen-mediated C-C bond formation. Remarkably, while hydroformylation is practiced on vast scale, systematic efforts toward the development of hydrogenative C-C couplings that extend beyond carbon monoxide coupling have remained absent from the literature. Ideally, it would be desirable to couple two or more organic molecules simply through their exposure to gaseous hydrogen in the presence of a metal catalyst. This goal represents the primary focus of research in our laboratory.
Representative Publications
"Phosphine Catalyzed a-Arylation of Enones Using Hypervalent Bismuth Reagents: Regiospecific Enolate Arylation via Nucleophilic Catalysis" J. Am. Chem. Soc. 126 (2004): 5350.
"Catalytic Enone Allylation via Concomitant Activation of Latent Nucleophilic and Electrophilic Partners: Merging Organic and Transition Metal Catalysis" J. Am. Chem. Soc. 125 (2003): 7758.
"Enantioselective Reductive Cyclization of 1,6-Enynes via Rhodium Catalyzed Asymmetric Hydrogenation: C-C Bond Formation Precedes Hydrogen Activation" J. Am. Chem. Soc. 127 (2005): 6174.
Barchuk, A.; Ngai, M.-Y.; Krische, M. J. "Enantioselective Iridium Catalyzed Imine Vinylation: Optically Enriched Allylic Amines via Alkyne-Imine Reductive Coupling Mediated by Hydrogen" J. Am. Chem. Soc. 129 (2007): 12644.
Skucas, E.; Kong, J.-R.; Krische, M. J. "Enantioselective Reductive Coupling of Acetylene to N-Arylsulfonyl Imines via Rhodium Catalyzed C-C Bond Forming Hydrogenation: (Z)-Dienyl Allylic Amines" J. Am. Chem. Soc. 129 (2007): 7242.
"Highly Enantioselective Direct Reductive Coupling of Conjugated Alkynes and a-Ketoesters via Rhodium Catalyzed Asymmetric Hydrogenation" J. Am. Chem. Soc. 128 (2006): 718.