Synlett 2012; 23(10): 1497-1500
DOI: 10.1055/s-0031-1290676
letter
© Georg Thieme Verlag Stuttgart · New York

Mild Oxidation of Benzylic Amines into Aldehydes Using an Oxidative Polonovski-Like Process

Samuel Desjardins
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec, Canada, Fax: +1(514)9874054   Email: canesi.sylvain@uqam.ca
,
Guillaume Jacquemot
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec, Canada, Fax: +1(514)9874054   Email: canesi.sylvain@uqam.ca
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Sylvain Canesi*
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec, Canada, Fax: +1(514)9874054   Email: canesi.sylvain@uqam.ca
› Author Affiliations
Further Information

Publication History

Received: 03 March 2012

Accepted after revision: 02 April 2012

Publication Date:
25 May 2012 (online)


Abstract

A chemoselective and environmentally benign oxidation of benzylic amines into aldehydes mediated by a hypervalent iodine reagent has been developed. This mild oxidative version of the ­Polonovski process may be selectively carried out in the presence of several functionalities including a free alcohol and provides new synthetic opportunities as a masked aldehyde segment.