4.7 Article

Copper-Catalyzed Chan-Lam Coupling of NH-Diaryl Sulfondiimines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 12, Pages 2040-2046

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200279

Keywords

Sulfondiimine; Chan-Lam coupling; Copper Catalysis; Chemoselectivity

Funding

  1. Guangdong-Joint Foundation of Shenzhen [2021B1515120046]
  2. Shenzhen Nobel Prize Scientists Laboratory Project [C17783101]
  3. Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
  4. National Natural Science Foundation of China [21865020]
  5. Program for Young Talents of Science and Technology in Universities of Inner Mongolia Autonomous Region (2019)

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Sulfondiimines, an underexplored scaffold in organic chemistry, have been synthesized efficiently through a copper-catalyzed method presented in this study. The synthesis allows the preparation of diversified sulfondiimines with various functional groups, and it was also used to generate an aza-analogue of an EphB4 inhibitor featuring a sulfondiimine-based pharmacophore.
Sulfondiimines, which contain a tetrasubstituted sulfur centre bearing two nitrogens and two carbon substituents, are a class of underexplored scaffolds in organic chemistry. Fascinated by some unique yet intriguing properties, sulfondiimines appear as leads in discovery industry, but the lack of efficient synthetic approaches holds back their further uptake by medicinal chemistry. Herein, a general and practical copper-catalyzed Chan-Lam coupling of NH-diaryl sulfondiimines with arylboronic acids is presented. A simple copper catalyst efficiently facilitated the highly chemoselective construction of C-N bond, allowing the preparation of a variety of N-arylated diaryl sulfondiimines in good yields under mild and environmentally benign conditions. An array of protecting groups on imine moieties were well tolerated, offering diversified accesses to NH,NAr-diaryl sulfondiimines, a class of versatile building blocks. Moreover, an aza-analogue of an EphB4 inhibitor featuring a sulfondiimine-based pharmacophore was generated employing our Chan-Lam coupling as the key step.

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