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Regioselective Semihydrogenation of Dienes

Thomas J. A. Graham, Thomas H. Poole, Charles N. Reese and Brian C. Goess*

*Department of Chemistry, Furman University, 3300 Poinsett Highway, Greenville, South Carolina 29613, United States, Email: brian.goessfurman.edu

T. J. A. Graham, T. H. Poole, C. N. Reese, B. C. Goess, J. Org. Chem., 2011, 76, 4132-4138.

DOI: 10.1021/jo200262r (free Supporting Information)


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Abstract

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

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Key Words

hydrogenation, hydrogen, Brown hydroboration, 2-methyl-2-nitrosopropane (MNP)


ID: J42-Y2011-1510