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Issue 90, 2014
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Retro-Claisen benzylation: direct use of benzyl alcohols in Pd-catalyzed couplings with nitriles

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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.

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

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Publication details

The article was received on 05 Sep 2014, accepted on 24 Sep 2014 and first published on 24 Sep 2014


Article type: Communication
DOI: 10.1039/C4CC07001A
Citation: Chem. Commun., 2014,50, 14045-14048
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    Retro-Claisen benzylation: direct use of benzyl alcohols in Pd-catalyzed couplings with nitriles

    T. Maji, K. Ramakumar and J. A. Tunge, Chem. Commun., 2014, 50, 14045
    DOI: 10.1039/C4CC07001A

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