Ph₂S₂–CaH₂ in N-methyl-2-pyrrolidone as an efficient protocol for chemoselective cleavage of aryl alkyl ethers

Abstract

CaH₂ was been found, for the first time, as a mild reducing agent to generate thiophenolate anion from Ph₂S₂ in N-methyl-2-pyrrolidone (NMP) for deprotection of aryl alkyl ethers. Excellent chemoselctivity was observed for substrates having chloro and nitro groups without displacement of the chlorine atom and the nitro group. Selective ether cleavage took place in the presence of α,β-unsaturated carbonyl and nitro groups without reduction and conjugate addition (to the α,β-unsaturated carbonyl group).