Modular Access to Sulfondiimidoyl Fluorides by NaH-Mediated Fluorination of Sulfenamides

Despite the significant applications of sulfondiimidoyl fluorides in medicinal chemistry, efficient methods for preparing these valuable fluorinated structures remain limited. Herein, we disclose a straightforward method for the modular synthesis of symmetric and unsymmetric sulfondiimidoyl fluorides through sequential amination and oxidation of sulfinimidoyl fluoride at room temperature. The resulting sulfondiimidoyl fluorides could be converted into a diverse array of sulfondiimines, sulfondiimidate esters, and sulfondiimidamides by SuFEx reaction. Moreover, a first proof of concept for an asymmetric protocol by employing a quinidine derivative catalyst is reported.