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.
Organic Letters
|May 14, 2026
Summary
Chemists developed stable sulfinylnitrene precursors for generating reactive intermediates. This enables efficient S-N bond formation and late-stage amine functionalization, creating valuable sulfonimidamides and sulfonimidates.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Sulfinylnitrene intermediates are highly reactive and difficult to handle.
- Existing methods for S-N bond formation often require harsh conditions or specialized reagents.
Purpose of the Study:
- To develop stable precursors for sulfinylnitrene generation.
- To establish a general and operationally simple method for S-N bond formation.
- To enable late-stage functionalization of amines.
Main Methods:
- Development of bench-stable sulfinylnitrene precursors.
- Chemoselective S-N bond cleavage under thermal or photolytic conditions.
- Reaction of generated intermediates with nucleophiles (N or O).
Main Results:
- Successful generation of reactive sulfinylnitrene intermediates from stable precursors.
- Formation of sulfonimidamides (privileged pharmacophore) and sulfonimidates (versatile intermediates).
- Demonstration of a general strategy for S-N bond formation without additives or pyrophoric reagents.
Conclusions:
- The developed precursors offer a safe and scalable route to sulfinylnitrene intermediates.
- This method provides a versatile approach for synthesizing sulfonimidamides and sulfonimidates.
- The transformation facilitates late-stage functionalization of amines, expanding synthetic possibilities.
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