Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols |
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Authors: | Marie Georgy Olivier Debleds Jean-Marc Campagne |
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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 |
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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. |
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