The Journal of Organic Chemistry

Palladium-catalyzed vinylic substitution with highly activated aryl halides

CB Ziegler Jr, RF Heck

Index: Ziegler,C.B.; Heck,R.F. Journal of Organic Chemistry, 1978 , vol. 43, p. 2941 - 2946

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Citation Number: 238

Abstract

Aryl bromides with strongly electron-donating substituents generally do not undergo the triphenylphosphinepalladium acetate catalyzed vinylic substitution reaction in acceptable yields. Competing formation of tetraaryl-phosphonium salts from the aryl bromide and, in some cases, reduction of the aryl bromide to the arene occur. Significant improvements in yield are often obtained when tri-o-tolylphosphine is used in place of triphenylphosphine. ...