A nickel-catalyzed carbon–sulfur cross-coupling reaction with disulfides enabled by mechanochemistry

Abstract

A novel and efficient thiolation method is described, which employs a Ni-catalyzed cross-coupling reaction between readily accessible disulfides and a variety of bromides, facilitated by ball milling. This Ni-catalyzed strategy exhibits remarkable functional group tolerance and a wide substrate compatibility, including the incorporation of acidic compounds. Additionally, a comprehensive investigation into the likely mechanism has been conducted, proposing a catalytic cycle involving multiple Ni oxidation states. The environmental impact of this approach has been assessed and compared favorably to traditional solution-phase methods. The utility of this transformation is underscored by its application in the synthesis of sulfur-containing organic compounds, emphasizing its high efficiency and eco-friendliness.