Safe, Scalable, Inexpensive, and Mild Nickel-Catalyzed Migita-Like C-S Cross-Couplings in Recyclable Water

A new approach to C-S couplings is reported that relies on nickel catalysis under mild conditions, enabled by micellar catalysis in recyclable water as the reaction medium. The protocol tolerates a wide range of heteroaromatic halides and thiols, including alkyl and heteroaryl thiols, leading to a variety of thioethers in good isolated yields. The method is scalable, results in low residual metal in the products, and is applicable to syntheses of targets in the pharmaceutical area. The procedure also features an associated low E Factor, suggesting a far more attractive entry than is otherwise currently available, especially those based on unsustainable loadings of Pd catalysts.

Automated summary

A new method of C-S coupling based on nickel catalysis in water with micellar catalysis has been reported, showing high isolated yields under mild conditions. It offers potential for scalability and low residual metal content, making it applicable to pharmaceutical synthesis targets. The associated low E Factor also suggests it may be a more attractive option compared to current methods using unsustainable Pd catalyst loadings.