Exploration on Metal-Catalytic Conversion of Sulfinyl Sulfones

The utilization of sulfinyl sulfones in transition-metal-catalyzed synthetic chemistry has rarely been investigated. Here we report the design and utilization of nickel-catalytic conversion of in situ-generated redox-active sulfinyl sulfones for reductive coupling with a wide variety of organic halides by the dual-role nickel catalyst and dual-role reductant Zn. Mechanistic studies disclose that the key design of such a reaction is the employment of redox-active sulfinyl sulfones, enabling the in situ generation of electrophilic sulfur reagents through zinc-induced reduction facilitated by the nickel catalyst. This strategy demonstrates good tolerance for a wide range of organic halides and functional groups. Furthermore, this method extends to meta-substituted functional diaryl sulfides, enabling the modification of complex bioactive molecules and the synthesis of thioether-containing drugs.

Automated summary

This study reports a novel synthetic method for the reductive coupling of organic halides with in situ-generated sulfinyl sulfones using a nickel catalyst and zinc reductant. The reaction exhibits broad substrate applicability and good functional group tolerance, making it suitable for the synthesis of complex organic molecules and thioether-containing drugs.