Unexpected catalyst for Wittig-type and dehalogenation reactions

J Org Chem. 2002 Jul 26;67(15):5320-6. doi: 10.1021/jo025693b.

Abstract

A novel catalyst 2 for Wittig-type and dehalogenation reactions was developed. In the presence of triphenyl phosphite, a wide variety of aldehydes could react with alpha-bromoacetates to afford alpha,beta-unsaturated esters or ketones in high yields with excellent E-stereoselectivity when 1-2 mol % of compound 2 was used. Compound 2 was also an effective catalyst for reductive dehalogenation of alpha-bromocarbonyl compounds. The mechanisms for the above reactions were also proposed.