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Synthesis

Arthur C. Cope Scholar: Michael J. Krische

by Mitch Jacoby
March 4, 2013 | A version of this story appeared in Volume 91, Issue 9

Krische
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Credit: Courtesy of Michael Krische
Michael Krische
Credit: Courtesy of Michael Krische

Reactions that form carbon-carbon bonds hold a place of special importance in chemical synthesis. Researchers who excel in this field develop a knack for applying these reactions masterfully and use them to synthesize complex products. But relatively few researchers develop broad, new families of C–C bond-forming reactions.

That’s exactly what ­Michael J. Krische, chemistry professor and Robert A. Welch Chair in Science at the University of Texas, Austin, has done in processes that merge the fields of catalytic hydrogenation and carbonyl addition. That accomplishment has earned him the respect and admiration of his colleagues.

Krische’s scientific research “is distinguished by remarkable inventiveness” with regard to chemical methodology, says Alois Fürstner, a specialist in organometallic chemistry and director of the Max Planck Institute for Coal Research in Mülheim, Germany. He adds that Krische’s contributions in the area of C–C bond-forming chemistry are characterized by “elegance of application,” especially to synthesizing bioactive target molecules, and stand out for their “significance and practicality.”

Krische is best known for developing C–C bond-forming hydrogenation reactions, which he describes as processes wherein two or more reactants are hydrogenated to form a single, more complex product. These reactions often generate products of carbonyl or imine addition. However, unlike corresponding classic carbonyl addition reactions, Krische’s by-product-free technique does not require stoichiometric quantities of preformed organometallic reagents. This body of work is recognized as the first systematic effort to exploit catalytic hydrogenation in C–C couplings beyond hydro­formylation, an established industrial process for converting alkenes to aldehydes.

In an extension of that work, Krische and coworkers developed related “C–C bond-forming transfer hydrogenations.” In these processes, the exchange of hydrogen between alcohols and unsaturated reactants generates aldehyde-organometal pairs that combine to give products of carbonyl addition. This straightforward approach to direct alcohol C–H functionalization is also by-product-free, and furthermore, it circumvents the redox manipulations often required to convert alcohols to aldehydes.

Describing these discoveries as “authentic examples of paradigm-shifting work,” Jeffrey S. Johnson, an asymmetric catalysis researcher at the University of North Carolina, Chapel Hill, says Krische has “fundamentally changed how chemists view hydrogenation and the chemistry of carbonyl addition.”

Krische, 46, obtained a bachelor’s degree in chemistry from the University of California, Berkeley, in 1989 and then conducted research as a Fulbright Fellow at Finland’s University of Helsinki. He earned a Ph.D. at Stanford University in 1996 and then served as a postdoctoral associate at Louis Pasteur University, Strasbourg, France. In 1999, Krische was appointed assistant professor of chemistry at the University of Texas, Austin, and was promoted directly to full professor in 2004.

Krische has received numerous awards in recognition of his contributions to chemistry. Among other accolades, he has been honored with the Presidential Green Chemistry Challenge Award, the GlaxoSmithKline Scholar Award, and the Mukaiyama Award from Japan’s Society of Synthetic Organic Chemistry, and he was named a Humboldt Foundation Senior Research Fellow. Krische has published some 175 scholarly articles and serves as an editor for Chemical Communications and Topics in Current Chemistry.

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