Heteroarylation of Sulfenamides for Modular Synthesis of Antimicrobial Sulfilimines via Sulfinimidoyl Fluoride Intermediates

We herein disclose a mild metal-free strategy for the construction of heteroaryl-derived sulfilimines. Central to this approach is the in situ generated sulfinimidoyl fluoride intermediate that exhibits an optimal balance of reactivity and stability for efficient S(IV)-derived SuFEx reactions with heteroarenes without Lewis acids or base additives. This protocol enables the rapid incorporation of a broad range of heteroarenes to afford diverse sulfilimine scaffolds with potent antimicrobial activities against plant pathogens.