Rhodium-catalyzed intramolecular silylation of unactivated C(sp3)-H bonds.

Org Lett

Division of Chemistry and Biotechnology, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Okayama 700-8530, Japan.

Published: January 2013

The treatment of a variety of hydrosilanes, each incorporating a benzylic C(sp(3))-H bond, with a rhodium catalyst resulted in intramolecular dehydrogenative silylation. This silylation reaction was found to occur at typically unreactive C(sp(3))-H bonds located at terminal positions on alkyl chains. Interestingly, the rhodium catalyst also promoted regioselective silylation at a site internal to an alkyl chain.

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http://dx.doi.org/10.1021/ol303353mDOI Listing

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