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

다국어 초록 (Multilingual Abstract)

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.
Aryl sulfides are easily made in water under mild conditions using a ligated base‐metal catalyst. A new Ni‐catalyzed C−S bond formation leading to functionalized products can now be obtained in good yields, with residual levels of metal contamination below FDA guidelines without additional processing.