Synthesis of Asymmetric Diaryl Sulfides via HI-Mediated C(sp)-H Sulfenylation of Arenes with Sodium Sulfinates.

A novel hydroiodic acid-promoted metal-free C(sp)-H sulfenylation of electron-rich arenes was developed using stable and easy-to-handle sodium sulfinates as sulfur sources. Diverse kinds of asymmetric aryl sulfides were afforded in good yields from various commercially available aromatic substrates under mild conditions. Comprehensive mechanistic experiments demonstrate that RSOSR and RSSR are the key intermediates responsible for the redox process.