Organic Letters 2009-06-04

Pd(O2CCF3)2/benzoquinone: a versatile catalyst system for the decarboxylative olefination of arene carboxylic acids.

Peng Hu, Jian Kan, Weiping Su, Maochun Hong

Index: Org. Lett. 11(11) , 2341-4, (2009)

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Abstract

A versatile palladium catalyst system was developed to effect the decarboxylative Heck coupling of a variety of arenecarboxylic acids with a wide range of olefins. The key to obtaining the efficient catalyst system is the use of 1-adamatanecarboxylic acid as additive. Alkyl-substituted olefins with coordinating groups were observed to provide significantly improved regioselectivity compared with other alkyl-substituted olefins lacking coordinating groups, and the acetate group of allylic ester was also tolerated in this reaction.