Carbon-Hydrogen Bond Activation Using Si, Ge, and Sn

Regents Of The University Of Michigan - Ann Arbor, Ann Arbor MI

Investigators

Abstract

This award in the Inorganic, Bioinorganic and Organometallic Chemistry program supports research by Professor Mark M. Banaszak-Holl at the University of Michigan to utilize silylene, germylene or stannylene together with an aryl halide for intermolecular CH-activation and to determine the mechanism of these new reactions. This new knowledge will be applied to processes that combine C-H activation with reactions important in the area of organic synthesis, such as the formation of carbon-carbon bonds using Stille cross-coupling. This chemistry represents the first example of CH-activation chemistry leading directly to the formation of bonds between carbon and group-14 elements. This new chemistry occurs by a poorly understood, radical reaction initiated by the interaction between the silylene, germlene, or silylene and the aryl halide that activates the ipso carbon of the phenyl ring to perform a hydrogen abstraction, while at the same time allowing formation of a new bond between the metalloid and the carbon of the activated hydrocarbon. The ability to activate the hydrocarbon and then immediately carry on the synthetic process to the next step would make some synthetic organic reactions more amenable to the environment. An additional environmental benefit is that this chemistry may help to make silicon-based synthetic reagents more accessible and thus help to replace the use of tin. This research program also interfaces with the Michigan Chemical Sciences at the Interface of Education (CSIE) and Research Experiences for Undergraduates (REU) programs for the training of our next generation of scientists including minority participants who are now in graduate school or hold faculty positions.