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

Samuel Desjardins; Guillaume Jacquemot; Sylvain Canesi

doi:10.1055/s-0031-1290676

Synlett, Table of Contents

Synlett 2012; 23(10): 1497-1500
DOI: 10.1055/s-0031-1290676

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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

,

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

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Abstract

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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.

Key words

hypervalent iodine - oxidation - amines - Polonovski - aromatic aldehydes

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References

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