A combined mechanistic and computational study of the gold(I)-catalyzed formation of substituted indenes

Pierrick Nun; Sylvain Gaillard; Albert Poater; Luigi Cavallo; Steven P Nolan

doi:10.1039/c0ob00758g

A combined mechanistic and computational study of the gold(I)-catalyzed formation of substituted indenes

Org Biomol Chem. 2011 Jan 7;9(1):101-4. doi: 10.1039/c0ob00758g. Epub 2010 Oct 20.

Authors

Pierrick Nun¹, Sylvain Gaillard, Albert Poater, Luigi Cavallo, Steven P Nolan

Affiliation

¹ EasStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, UK KY16 9ST.

PMID: 20963218
DOI: 10.1039/c0ob00758g

Abstract

Substituted indenes can be prepared after a sequence [1,3] O-acyl shift-hydroarylation-[1,3] O-acyl shift. Each step is catalyzed by a cationic NHC-Gold(I) species generated in situ after reaction between [(IPr)AuOH] and HBF(4)·OEt(2). This interesting silver-free way is fully supported by a computational study justifying the formation of each intermediate.