Room-Temperature C-H Bromination and Iodination with Sodium Bromide and Sodium Iodide Using N-Fluorobenzenesulfonimide as an Oxidant

A transition-metal-free electrophilic bromination and iodination of arene through C-H cleavage at room temperature has been developed in excellent to quantitative yields with broad arene scope and good regioselectivity, in which environment-benign and readily available sodium halides, NaBr or NaI, were employed as halogen sources in accompany with N-fluorobenzenesulfonimide (NFSI) as an oxidant. Studies have also demonstrated that, in this air- and moisture-resistant scalable halogenation under mild conditions, the oxidant NFSI is reduced to dibenzenesulfonimide which usually serves as the starting material for the preparation of NFSI, rendering this facile and versatile protocol promising potentials for future applications in organic synthesis.