The Journal of Organic Chemistry

Highly regioselective thiocarbonylation of allylic alcohols with thiols and carbon monoxide catalyzed by palladium complexes: a new and efficient route to β, γ- …

WJ Xiao, H Alper

Index: Xiao, Wen-Jing; Alper, Howard Journal of Organic Chemistry, 1998 , vol. 63, # 22 p. 7939 - 7944

Full Text: HTML

Citation Number: 39

Abstract

The reaction of allylic alcohols with thiols and carbon monoxide in the presence of catalytic quantities of Pd (OAc) 2 (3 mol%), triphenylphosphine (12 mol%), and p-TsOH (5 mol%) leads to a novel thiocarbonylation to afford β, γ-unsaturated thioesters in good to excellent yields. Other palladium catalyst systems such as Pd2 (dba) 3⊙ CHCl3-PPh3-p-TsOH, Pd (PPh3) 4-p-TsOH, and Pd (OAc) 2-dppb-p-TsOH are also effective for this transformation. ...