Special Inorganic Seminar: B. Keith Keitz, Berkeley

January 06, 2014 - 03:00 PM - 04:00 PM

Dr. B. Keith Keitz
University of California, Berkeley


2000 Vagelos

Z-Selective Ruthenium Metathesis Catalysts

Stereocontrol in olefin metathesis is an ongoing challenge because of the thermodynamic preference for E-olefin products. Here, we describe the preparation of new ruthenium metathesis catalysts formed via the carboxylate-induced C-H activation of an N-heterocyclic carbene ligand. These catalysts adopt a unique geometry that results in unprecedented selectivity for Z-olefins in a variety of reactions including cross-metathesis, macrocyclic ring-closing metathesis, and ring-opening metathesis polymerization. Moreover, we show that they are effective at low catalyst loadings and can survive prolonged exposure to dioxygen, water, and a variety of common functional groups. Finally, we present extensive experimental and theoretical investigations into the mechanism of this new class of ruthenium metathesis catalysts and the origin of their remarkable Z-selectivity.

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