Synthesis of benzo[c]chromen-6-ones via novel cyclic aryl-Pd(II)-ester enolate intermediates

Authors

Stephen R. Taylor, University of Wollongong
Alison T. Ung, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow

RIS ID

21132

Publication Details

Taylor, S. R., Ung, A. T. & Pyne, S. G. (2007). Synthesis of benzo[c]chromen-6-ones via novel cyclic aryl-Pd(II)-ester enolate intermediates. Tetrahedron, (63), 10889-10895.

Abstract

The examination of the palladium catalysed arylation reactions of mono-iodo derivatives of the phenyl and benzyl esters of benzoic acid, phenylacetic acid and dehydrocinnamic acid has resulted in the formation of benzo[c]chromen-6-ones, unexpected cinnamate and succinate products and diphenyl dimers. Many of these products can be rationalized as arising from novel cyclic ArPd(II)-enolate intermediates, formed by intramolecular C-H activation by ArPd(II).