Design of a Bilateral Disulfurating Reagent for Unsymmetrical Polysulfidation

Abstract

In this study, we designed a bilateral disulfurating reagent via SÀ S motif "snip and stitch" processes, allowing diverse functional groups to be bridged via SÀ S bonds. The reagent is readily synthesized in high yield using a one-step reaction from easily available starting materials and is air-stable. With this reagent, diverse electrophiles including inactivated alkyl Cl/Br/I/OMs and benzyl chloride were sequentially installed on either side of the SÀ S motif. Natural products, agrochemicals, and pharmaceuticals can be successively cross-linked with SÀ S bonds. Notably, the disulfurating reagent can be used in cyclic disulfide synthesis. At last, some desired products of this work showed good antibacterial activities, which could be employed as novel candidates to control plant pathogenic bacteria.

Copper-Catalyzed Chemoselective Coupling of N-Dithiophthalimides and Alkyl Halides: Synthesis of Unsymmetrical Disulfides and Sulfides

“…The unique reactivity of tetrasulfides has gradually attracted attention , (Scheme d). In recent years, the design and synthesis of bilateral sulfur reagents have developed and become a more effective and flexible method for synthesizing disulfides (Scheme e).…”