Chem Asian J. 2022 Nov 29. doi: 10.1002/asia.202201078. Online ahead of print.

ABSTRACT

Benzyl phenyl sulfide is a kind of important chemicals with wide usages, which are mainly prepared through a nucleophilic reaction of thiophenol with benzyl chlorides or benzyl alcohols, suffering from inherent drawbacks, such as low efficiency, requirements for equivalent acid or base catalysts and formation of harmful byproducts and wastes. Herein, we report a green route to access various benzyl phenyl sulfide derivatives in good to excellent yields under mild conditions via the reaction of thioanisoles with benzyl alcohols over ionic liquid 1-propylsulfonate-3-methylimidazolium trifluoromethanesulfonate ([SO3HPrMIm][OTf]). Mechanism investigation indicates that the synergic effect of cation and anion of [SO3HPrMIm][OTf] activates thioanisoles and benzyl alcohols via hydrogen bonding, thus catalyzes the dehydration of benzyl alcohol to dibenzyl ether and the subsequent metathesis reaction between dibenzyl ether and benzyl phenyl sulfide, finally generating benzyl phenyl sulfide derivatives. This is a simple, highly efficient, and green approach to produce benzyl phenyl sulfide derivatives, which may have promising application potentials.

PMID:36445934 | DOI:10.1002/asia.202201078