Rhodium-catalyzed cyclization reaction of 1,6-enynes with arylboronic acids through beta-hydride elimination/hydrorhodation sequence

Chem Asian J. 2008 Jun 2;3(6):1035-40. doi: 10.1002/asia.200700407.

Abstract

Methoxy-substituted 1,6-enynes react with arylboronic acids in the presence of a rhodium(I) complex to give arylated cyclization products. This occurs by a multi-step mechanism consisting of rhodium/boron transmetalation, intermolecular carborhodation, intramolecular carborhodation, beta-hydride elimination, hydrorhodation, and beta-oxygen elimination. A shift of the position of a carbon-carbon double bond is observed, suggesting that the beta-hydride elimination/hydrorhodation process is repeatedly taking place.