One-Pot Oxidative Conversion of Alcohols into Nitriles by Using a TEMPO/PhI(OAc)₂/NH₄OAc System

Jean-Michel Vatèle*

*Université Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), UMR 5246 CNRS, bât. Raulin, 43, Bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France, Email: vateleuniv-lyon1.fr

J.-M. Vatèle, Synlett, 2014, 25, 1275-1278.

DOI: 10.1055/s-0033-1341124

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Abstract

A direct conversion of a wide range of aliphatic, benzylic, heteroaromatic, allylic, and propargyl alcohols into nitriles with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), iodosobenzene diacetate, and ammonium acetate as a nitrogen source proceeds through an oxidation-imination-aldimine oxidation sequence in situ. Highly chemoselective ammoxidation of primary alcohols in the presence of secondary alcohols was also achieved.

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Key Words

alcohols, chemoselectivity, nitriles, oxidation, TEMPO, PIDA

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ID: J60-Y2014