Sulfuroxygen interaction-controlled (Z)-selective anti-Markovnikov vinyl sulfides.

The sulfur oxygen (SO) interaction was used herein to obtain (Z)-selective anti-Markovnikov vinyl sulfides from the addition of thiyl radicals to terminal alkynes. DFT calculations predicted that SO interaction originated from the delocalization of the lone-pair of the carbonyl oxygen to the adjacent σ* orbital of the S atom of C-S.