Passerini Three-Component Reaction of Alcohols under Catalytic Aerobic Oxidative Conditions

Julien Brioche, Géraldine Masson* and Jieping Zhu*

*Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France, Email: zhuicsn.cnrs-gif.fr, massonicsn.cnrs-gif.fr

J. Brioche, G. Masson, J. Zhu, Org. Lett., 2010, 12, 1432-1435.

DOI: 10.1021/ol100012y

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Abstract

Passerini three-component reaction under catalytic aerobic conditions allows the conversion of alcohols instead of aldehydes. The reaction of alcohols, isocyanides, and carboxylic acids in toluene in the presence of a catalytic amount of cupric chloride, NaNO₂, and TEMPO afforded, under an oxygen atmosphere, the P-3CR adducts in good yields.

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Key Words

Passerini Reaction, TEMPO, Oxygen, Multicomponent Reactions

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ID: J54-Y2010-0860