A vinylic Rosenmund-von Braun reaction: practical synthesis of acrylonitriles.

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.