Rapid Access to N-Protected Sulfonimidoyl Fluorides: Divergent Synthesis of Sulfonamides and Sulfonimidamides

Herein we report a practical and efficient copper-catalyzed approach for the conversion of various arenediazonium salts to the corresponding N-protected sulfonimidoyl fluorides. This operationally simple protocol tolerates a wide range of functional groups and can be applied to the late-stage modification of complex bioactive molecules. Furthermore, pharmaceutically important primary sulfonamides and sulfonimidamides derived from these valuable N-protected sulfonimidoyl fluoride units were prepared in minimal synthetic steps.

Automated summary

In this study, a practical and efficient copper-catalyzed method was reported for the conversion of various arenediazonium salts to N-protected sulfonimidoyl fluorides. This protocol tolerates a wide range of functional groups and is suitable for late-stage modification of complex bioactive molecules, leading to the synthesis of pharmaceutically important primary sulfonamides and sulfonimidamides in minimal synthetic steps.