Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo [b] furans and benzo [b] thiophenes

MC Willis, D Taylor, AT Gillmore

Index: Willis, Michael C.; Taylor, Dawn; Gillmore, Adam T. Tetrahedron, 2006 , vol. 62, # 49 p. 11513 - 11520

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Citation Number: 87

Abstract

Enolates derived from α-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C– O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd2 (dba) 3 and the ligand DPEphos effects the key bond formation to deliver a variety of substituted products from both cyclic and acyclic precursors. The analogous thio-ketones undergo C–S bond formation using identical reaction conditions and are converted to ...