Sulfinylnitrenes via Chemoselective S-N Bond Cleavage: Design, Synthesis, and Applications
Prakash Kafle1, Rishav Mukherjee1, Shuhei Yasuda1
1Department of Chemistry and Biochemistry, University of Oklahoma, 101 Stephenson Parkway, Norman, Oklahoma 73019-5251, United States.
Abstract:
Herein, we report the development of bench-stable, scalable sulfinylnitrene precursors that enable the generation of reactive sulfinylnitrene intermediates via chemoselective S-N bond cleavage under thermal or photolytic conditions, without additives or pyrophoric reagents. These intermediates react with nucleophiles (N or O) to afford sulfonimidamides, a privileged pharmacophore, or sulfonimidates, a versatile intermediate in deoxygenating reactions. This operationally simple transformation provides a general strategy for S-N bond formation and enables late-stage functionalization of amines.
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