Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


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.

see article for more examples



Key Words

alcohols, chemoselectivity, nitriles, oxidation, TEMPO, PIDA


ID: J60-Y2014