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Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols
Authors:Marie Georgy  Olivier Debleds  Jean-Marc Campagne
Institution:a Institut de Chimie des Substances Naturelles, UPR 2301, Avenue de la Terrasse, 91198 Gif sur Yvette, France
b Institut Charles Gerhardt Montpellier, UMR 5253 CNRS-UM2-UM1-ENSCM, 8 rue de l'Ecole Normale, 34296 Montpellier, France
Abstract:Gold-catalyzed nucleophilic substitution of propargylic alcohols with various nucleophiles (allylsilane, electron-rich aromatics, alcohols, thiols, hydrides, 1,3-dicarbonyl derivatives, sulfonamides) is described under very mild conditions (room temperature in dichloromethane). Preliminary mechanistic investigations suggest a mechanism through a carbocation intermediate. Nucleophilic substitutions on allylic and benzylic alcohols are also described.
Keywords:
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