Development of an Anomalous Heck Reaction: Skeletal Rearrangement of Divinyl and Enyne Carbinols

JM Ndungu, KK Larson, R Sarpong

Index: Ndungu, J. Maina; Larson, Kimberly K.; Sarpong, Richmond Organic Letters, 2005 , vol. 7, # 26 p. 5845 - 5848

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Citation Number: 16

Abstract

A general set of conditions that achieves the union of aryl halides and divinyl or enyne carbinols to afford tri-or tetrasubstituted olefins in good yields (up to 83%) is described. The mechanism by which this proceeds is believed to involve the intermediacy of a cyclopropanol, followed by a novel skeletal reorganization. The ability to suppress β-hydride elimination of organopalladium intermediates appears to be critical to the success of these ...