Copper‐Catalyzed Chan‐Lam Coupling of NH‐Diaryl Sulfondiimines
Yangyang Wang, Tingting Meng, Shuaisong Su, Limin Han, Ning Zhu, Tiezheng Jia
Abstract
Abstract 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 N H‐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 N H, N Ar‐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. magnified image