Journal of the American Chemical Society 2009-10-14

N-heterocyclic carbene-catalyzed hydroacylation of unactivated double bonds.

Keiichi Hirano, Akkattu T Biju, Isabel Piel, Frank Glorius

Index: J. Am. Chem. Soc. 131 , 14190-14190, (2009)

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Abstract

An intramolecular N-heterocyclic carbene (NHC)-catalyzed hydroacylation of unactivated double bonds is reported. Systematic variation of the catalyst structure revealed an N-mesitylthiazolylidene annulated with a seven-membered ring to be especially reactive. This NHC enables a unique C-C bond-forming reaction to afford substituted chroman-4-ones in moderate to excellent yields, even ones containing all-carbon quaternary centers.