This review presents an overview of the reductive decyanation reaction with a special interest for recent developments. This transformation allows synthetic chemists to take advantages of the nitrile functional group before its removal. Mechanistic details and applications to organic synthesis are provided.

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This review describes the preparation and chemical reactivity of 2-chromanols. These derivatives appear as interesting intermediates in the synthesis of various natural products and biologically active compounds.

This review focuses on the Bruylants reaction, namely the substitution with Grignard reagents of the cyano group in -aminonitriles. This reaction goes through an iminium ion intermediate and proceeds with excellent stereoselectivities. The extension to organozinc reagents has been successfully applied. Triazoles such as benzotriazole and especially 1,2,3-triazole appear as relevant substitutes for the cyano leaving group. An alternative pathway for substitution of the cyano group involves an -alkylation-decyanation sequence. Selected applications in organic synthesis are proposed.

Review: 103 refs.