Regioselective semihydrogenation of dienes.

J Org Chem

Department of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, United States.

Published: May 2011

A one-pot, three-step strategy for the regioselective semihydrogenation of dienes is described. This procedure uses 9-BBN-H as a temporary protective group for alkenes. Yields range from 55% to 95%, and the reaction is tolerant of a variety of common functional groups. Additionally, the final elimination step of the sequence can be replaced with a peroxide-mediated alkylborane oxidation, generating regioselectively semihydrogenated product alcohols.

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http://dx.doi.org/10.1021/jo200262rDOI Listing

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