FACILE ACYLATION OF NUCLEOPHILES WITH OXIDIZING AGENT-THIOL ESTER PAIRS

Abstract Thiol esters (MeCO-SPh, 2,4,6-Me3C6H2CO-SMe, p-MeC6H4SO2-SMe) were found to function as good acylating agents for nucleophiles(MeOH, t-BuOH, PhOH, PhNH2, Cl−, Br−) when mixed with oxidizing agents (m-ClC6H4CO3H, N-bromosuccinimide) in CH2Cl2 solution. Thiol esters and NBS appear to form a sulfurane as the reactive intermediate.