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Modular Sulfondiimine Synthesis Using a Stable Sulfinylamine Reagent
Ze-Xin Zhang1, Thomas Q Davies1, Michael C Willis1
1Department of Chemistry, Chemistry Research Laboratory , University of Oxford , Mansfield Road , Oxford OX1 3TA , United Kingdom.
This study introduces a novel synthesis for sulfondiimines, crucial in discovery chemistry. The new method avoids hazardous reagents and uses readily available starting materials for efficient production.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
Background:
- Sulfondiimines are valuable in discovery chemistry but lack efficient synthetic routes.
- Current methods use hazardous reagents and sulfide/thiol starting materials.
Purpose of the Study:
- To develop a new, safer, and more versatile method for sulfondiimine synthesis.
- To enable access to diverse sulfondiimine structures with orthogonal N-functionalization.
Main Methods:
- Utilized Grignard reagents and a sulfinylamine reagent for sulfondiimine synthesis.
- Employed Lewis acid-mediated assembly to form sulfilimine intermediates.
- Developed a rhodium-catalyzed imination for diverse sulfondiimine generation.
Main Results:
- Efficient synthesis of sulfondiimine precursors (sulfilimines) from non-sulfide/thiol starting materials.
- Access to a wide array of sulfondiimines with orthogonal N-functionalization.
- Demonstrated selective manipulation of both N-atoms for mono- and difunctionalized products.
- Described oxidation of sulfilimines as a route to sulfoximines.
Conclusions:
- The new method provides a significant advancement in sulfondiimine synthesis.
- Offers a safer and more flexible alternative to existing protocols.
- Expands the synthetic utility of sulfondiimines in discovery chemistry.
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