[(NHC)AuI]-catalyzed rearrangement of allylic acetates

Org Lett. 2007 Jul 5;9(14):2653-6. doi: 10.1021/ol070843w. Epub 2007 Jun 8.

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.