Thiol-free synthesized and sustainable thiolating synthons for nickel-catalyzed reductive assembly of sulfides with high efficiency

Unsymmetrical sulfides are widely found in the pharmaceutical industry, organic synthesis, and materials science. As a result, it will be of great significance to discover mild and efficient methodologies and electrophilic sulfur transfer reagents, avoiding the general employment of odorous and toxic thiols. Herein, we present a highly efficient nickel-catalyzed cross-electrophile coupling of organic halides with thiol-free synthesized N-thiophthalimides as direct thiolating surrogates. This practical strategy features extremely low catalyst loading, good functional group tolerance and diverse downstream synthesis, enabling the construction of a broad range of sulfides under base-free conditions. Notably, a modified and more efficient reductive thiolation of disulfides was developed by employing our mild reaction conditions.

Automated summary

A highly efficient cross-electrophile coupling of organic halides with thiol-free synthesized N-thiophthalimides as direct thiolating surrogates was presented. This strategy avoids the use of odorous and toxic thiols and features low catalyst loading, good functional group tolerance, and diverse downstream synthesis.