Micelle Enhanced Auto-Oxidative Hydroxysulfenylation of Alkenes

The organic solvent free auto-oxidative radical hydroxysulfenylation of olefins in a micellar system was presented which enables the simultaneous C–O and C–S couplings to be performed in a green and sustainable manner, using oxygen as the only oxidant. Particularly noteworthy is the finding that micelle was attributed to enhancing both selectivity and reactivity for the C–S coupling. Meanwhile, the radical mechanism was determined, and distinguished from a traditional nucleophilic addition mechanism in a water-like system.