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[(NHC)Au^I]-Catalyzed Rearrangement of Allylic Acetates

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Nicolas Marion, Ronan Gealageas, and Steven P. Nolan*

Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain

Org. Lett., 2007, 9 (14), pp 2653–2656

DOI: 10.1021/ol070843w

Publication Date (Web): June 8, 2007

Section:

Aliphatic Compounds

Abstract

[(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.

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