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 (CX 4 ) 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 CCl 4 are the advantages of this protocol.