(NHC)CuH-Catalyzed Entry to Allenes via Propargylic Carbonate S_N2'-Reductions

Carl Deutsch, Bruce H. Lipshutz and Norbert Krause*

*Organic Chemistry, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany, Email: norbert.krausetu-dortmund.de

C. Deutsch, B. H. Lipshutz, N. Krause, Org. Lett., 2009, 11, 5010-5012.

DOI: 10.1021/ol901868m

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Abstract

A copper hydride-catalyzed S_N2′-reduction of propargylic carbonates provides functionalized allenes in good yields. The method takes advantage of the stabilizing effect of NHC ligands on CuH and offers high reactivity, stereoselectivity, and functional group tolerance.

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Key Words

Allenes, Copper Hydride, PMHS

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ID: J54-Y2009-3240