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(NHC)CuH-Catalyzed Entry to Allenes via Propargylic Carbonate SN2′-Reductions

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Organic Chemistry, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, Germany, and Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106
†Dortmund University of Technology.
‡University of California, Santa Barbara.
Cite this: Org. Lett. 2009, 11, 21, 5010–5012
Publication Date (Web):October 5, 2009
Copyright © 2009 American Chemical Society

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    Abstract Image

    The copper hydride-catalyzed SN2′-reduction of propargylic carbonates provides an efficient route to functionalized allenes. The method takes advantage of the stabilizing effect of NHC ligands on CuH and combines high reactivity and stereoselectivity with excellent tolerance toward reactive functionalities.

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