K2S2O8 promoted dehydrative cross-coupling between α,α-disubstituted allylic alcohols and thiophenols/thiols

Allyl sulfides are important organosulfur compounds. K2S2O8 promoted dehydrative cross-coupling between alpha,alpha-disubstituted allylic alcohols and thiophenols/thiols is demonstrated for the first time, which resulted in a wide range of allyl sulfides in good to high yields. Note that this metal-free synthetic method features broad substrate scopes; in addition to thiophenols and thiols, pyrazole, sodium benzenesulfinate, and sodium trifluoromethanesulfinate were also tolerated. Mechanistic studies revealed that a radical addition process might be involved in the reaction.

Automated summary

This study demonstrated for the first time that K2S2O8 promoted dehydrative cross-coupling reaction can synthesize a wide range of allyl sulfides, with broad substrate scopes and tolerance to various substrates, possibly involving a radical addition process.