Retro-Claisen benzylation: direct use of benzyl alcohols in Pd-catalyzed couplings with nitriles

Literature Information

Publication Date 2014-09-24
DOI 10.1039/C4CC07001A
Impact Factor 6.222
Authors

Tapan Maji, Kinthada Ramakumar, Jon A. Tunge


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Abstract

A new strategy has been developed for the benzylation of nitriles directly from benzyl alcohols. In this process benzyl alcohols undergo retro-Claisen activation with cyanoacetic esters to generate an active electrophile and a carbanionic nucleophile. In the presence of Pd(0) these intermediates undergo catalytic coupling to generate a new C–C bond, resulting in the formation of phenyl propionitriles.

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