<i>N</i> ‐Alkoxysulfurdiimide Reagents for the One‐Step Modular Synthesis of Primary Sulfonimidamides

Abstract

ABSTRACT Sulfonimidamides are an emerging motif in medicinal chemistry; however, current synthetic routes often require multistep reaction sequences, deprotection steps, and lack the modularity needed for rapid and diverse library synthesis. Here, we describe the synthesis and application of previously unexplored N ‐alkoxysulfurdiimide reagents for the direct, one‐step preparation of primary NH 2 ‐sulfonimidamides. By modulating the choice of N ‐substituent, N ‐alkoxysulfurdiimide reagents can be designed to deliver different product distributions. This reactivity correlates with the electron density at sulfur, as inferred from 13 C NMR chemical shifts from the reagents. This tunability can be exploited to design reagents with improved compatibility across organometallic reagents, enabling the preparation of a diverse set of primary NH 2 ‐sulfonimidamides.