Synthesis of functionalized sulfilimines via iron-catalyzed sulfur alkylation of sulfenamides with diazo compounds

An efficient iron-catalyzed sulfur alkylation of sulfenamides with 2,2,2-trifluorodiazoethane is developed. The reaction proceeds smoothly at room temperature in an open flask, enabling the rapid synthesis of trifluoromethylated sulfilimines in moderate to good yields with broad functional group tolerance. In addition, this operationally simple protocol could also be applied to access cyano- and phosphonyl-functionalized sulfilimines using diazoacetonitrile or diazomethylphosphonate.