Sulfinamides (R−S(=O)−NR₂) are used, e.g., in medicinal chemistry or organic synthesis. They can serve as synthetic precursors for a wide variety of sulfur-containing organic compounds and also have uses as ligands or chiral auxiliaries. Existing methods or the synthesis of sulfinamides can have drawbacks such as low atom economy, a need for unstable reagents, or harsh reaction conditions.

Yi Wei, Xiao-Qiang Hu, South-Central Minzu University, Wuhan, China, and colleagues have developed a method for the iron-catalyzed photochemical sulfinamidation of hydrocarbons with N-sulfinylamines to give sulfinamides (example product pictured). The team reacted a range of N-sulfinylamines with different aliphatic hydrocarbons using FeCl₃ as a catalyst and acetonitrile as a solvent under irradiation with LED lights (390 nm) and an N₂ atmosphere. The reactions were performed at room temperature.

Under these conditions, the desired sulfinamides were obtained in moderate to high yields. The team also performed the reaction on a gram scale, obtaining a yield of 67 %. The approach was also suitable for the late-stage functionalization of drug-like molecules, and the work could have applications in drug discovery.

• Iron-Catalyzed Photochemical Synthesis of Sulfinamides from Aliphatic Hydrocarbons and Sulfinylamines,
  Guang-Da Xia, Run Li, Long Zhang, Yi Wei, Xiao-Qiang Hu,
  Org. Lett. 2024.
  https://doi.org/10.1021/acs.orglett.4c00612