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

Abstract

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.