Student Hosted Colloquia: Professor John Hartwig, UC Berkeley
"Catalytic Functionalization Reactions by Organometallic Catalysts in a Flask and in a Cell"
Host: Zach Gentry
About the Seminar
Our group has sought the functionalization of C-H and C=C bonds catalyzed by transition-metal complexes with control of site-selectivity, regioselectivity and enantioselectivity. We have reported widely practiced functionalizations of aromatic C-H bonds with boron reagents and recently discovered catalysts that functionalize primary alkyl C-H bonds under practical conditions. In parallel, we have sought to create artificial metalloenzymes that contain catalysts from the laboratory as the active site for regioselective and stereoselective functionalizations of C-H and C=C bonds. This lecture will present selected examples from and mechanistic analysis of our functionalizations of C-H bonds at primary, secondary, and tertiary positions with small-molecule catalysts, along with the creation of artificial metalloenzymes that catalyze organometallic reactions within whole cells and within biosynthetic pathways of these cells to produce unnatural products.
About the Speaker
John Hartwig received his A.B. from Princeton University. He received his Ph.D. from U.C. Berkeley with Bob Bergman and Richard Andersen and conducted a postdoctoral fellowship at MIT with Stephen Lippard. In 1992 he began his independent career at Yale University and became the Irenée P. DuPont Professor in 2004. In 2006, he moved to the University of Illinois, where he was the Kenneth L. Rinehart Jr. Professor of Chemistry. In 2011, he returned to U.C. Berkeley as the Henry Rapoport Professor.
Professor Hartwig's research focuses on discovering and understanding new reactions for organic synthesis catalyzed by transition metal complexes. He is well known for contributions to widely practiced cross-coupling chemistry that forms arylamines, aryl ethers, aryl sulfides, and α-aryl carbonyl compounds and for discovering practical C-H bond functionalization reactions. He has also contributed to the catalytic hydrofunctionalization of alkenes, asymmetric allylic substitution, and methods to functionalize and unravel polyolefins. Recently he has published on reactions catalyzed by artificial metalloenzymes that combine the reactivity of transition-metal catalysts with the selectivity and evolutionary potential of enzymes. He has focused on the mechanism and fundamental organometallic chemistry that underpins them, including studies on reductive eliminations to form carbon-heteroatom bonds, oxidative addition of N-H bonds, and olefin insertions into amides and alkoxides. He is the author of the textbook “Organotransition Metal Chemistry: From Bonding to Catalysis” and has received among his awards the Nagoya Gold Medal, the Arthur C. Cope Award, the Tetrahedron Prize in Organic Synthesis, and the Wolf Prize in Chemistry.
Image Credit: Michael Barnes