Coppola et al. Org Lett. 2013;15(13):3388-91. Remote aryl cyanation via isocyanide-cyanide rearrangement on tosylmethyl isocyanide derivatives.

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Remote aryl cyanation via isocyanide-cyanide rearrangement on tosylmethyl isocyanide derivatives.

Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala, 28871 - Alcala de Henares, Madrid, Spain.

Abstract

The reaction of alkyl tosylmethyl isocyanides and 2-bromobenzyl bromides in the presence of t-BuLi gives rise to a cascade reaction to give unexpected 2-substituted 2,3-dihydro-1H-indenimines which, upon treatment with t-BuOK, rearrange to 2-vinylbenzonitriles in high overall yields. This simple procedure represents a new approach to the synthesis of aromatic nitriles via isocyanide-cyanide interconversion.

graphical abstract