1,2-Difunctionalization of Aryne with Sulfenamide and Organohalide: Mild and Metal-Free Access to S-(o-Halo)aryl Sulfilimine

A mild and metal-free approach has been developed for 1,2-difunctionalization of aryne using sulfenamides as a nucleophile and a halogen source (CX4) as an electrophile to synthesize S-(o-halo)aryl sulfilimines. The late-stage functionalizations of halide handles via Suzuki–Miyaura and Buchwald–Hartwig reactions exhibit the synthetic utilities of the products. The chemoselectivity, regioselectivity, rapidity, and use of economical CCl4 are the advantages of this protocol.