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

Nicolas Marion, Ronan Gealageas and Steven P. Nolan*

*School of Chemistry, University of St Andrews, St Andrews KY16 9ST, U.K., Email: sn17st-andrews.ac.uk

N. Marion, R. Gealageas, S. P. Nolan, Org. Lett., 2007, 9, 2653-2656.

DOI: 10.1021/ol070843w

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Abstract

Gold N-heterocyclic carbene complexes, in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The steric hindrance of the ligand bound to gold was found crucial as only bulky ligands permitted the isomerization.

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proposed mechanism

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Key Words

Overman Rearrangement, Allylic Alcohols, Microwave Synthesis

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ID: J54-Y2007-2150