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Issue 80, 2014
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A vinylic Rosenmund–von Braun reaction: practical synthesis of acrylonitriles

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Abstract

An efficient system based on acetone cyanohydrin and catalytic amounts of copper(I) iodide and 1,10-phenanthroline is reported for the cyanation of alkenyl iodides. A wide range of polysubstituted acrylonitriles could be obtained in fair to good yields and with complete retention of the geometry of the double bond. This extension of the Rosenmund–von Braun reaction also enabled a straightforward formal synthesis of the naturally occurring acrylonitrile alliarinoside.

Graphical abstract: A vinylic Rosenmund–von Braun reaction: practical synthesis of acrylonitriles

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Publication details

The article was received on 18 Jul 2014, accepted on 15 Aug 2014 and first published on 18 Aug 2014


Article type: Communication
DOI: 10.1039/C4CC05557H
Citation: Chem. Commun., 2014,50, 11907-11910
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    A vinylic Rosenmund–von Braun reaction: practical synthesis of acrylonitriles

    A. Pradal and G. Evano, Chem. Commun., 2014, 50, 11907
    DOI: 10.1039/C4CC05557H

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