Mechanism of the [(nhc)aui]-catalyzed rearrangement of allylic acetates. A DFT study

Christophe Gourlaouen, Nicolas Marion, Steven P. Nolan, Feliu Maseras

Research output: Contribution to journalArticleResearchpeer-review

39 Citations (Scopus)

Abstract

The DFT study of the mechanism of the rearrangement of H 2C=CHC(CH3)OCOCH3 to (CH3)(H)C= CHCH2OCOCH3 catalyzed by [(NHC)Au]+ (NHC= N-heterocyclic carbene) shows that a low energy path exists, with a barrier of 14.2 kcal.mol-1, going through a six-membered ring acetoxonium intermediate and where gold coordinates one of the carbon atoms in the alkene system. The qualitative features of the mechanism are not affected by the introduction of other NHC ligands, counterions, or solvation effects. © 2009 American Chemical Society.
Original languageEnglish
Pages (from-to)81-84
JournalOrganic Letters
Volume11
Issue number1
DOIs
Publication statusPublished - 1 Jan 2009

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