Rapid Mechanochemical Synthesis of Azosulfones

Azosulfones represent a potent and stable surrogate for diazonium salts. Their wide application in C–H functionalizations catalyzed by transition metals and visible light is well‐known in organic chemistry. Here, a single‐step mechanochemical synthesis of azosulfones is reported, starting from readily available precursors, which has high conversion efficacy −80%–99% isolated yields are obtained in most cases. A substrate scope of 30 different compounds is obtained. This method requires no solvent, it is quick and has potential in terms of scalability and tolerance toward a broad range of functional groups, which makes it attractive for synthesis. Spectroscopic and computational studies are performed to explain the observed reactivity patterns.