Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols

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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. © 2008 Elsevier Ltd. All rights reserved.

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Georgy, M., Boucard, V., Debleds, O., Zotto, C. D., & Campagne, J. M. (2009). Gold(III)-catalyzed direct nucleophilic substitution of propargylic alcohols. Tetrahedron, 65(9), 1758–1766. https://doi.org/10.1016/j.tet.2008.12.051

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