Construction of Biaryl Sulfonamides via Pd(II)-Catalyzed Cross-Coupling of C(sp2)-H Bonds with Iodobenzenesulfonamides.

Abstract

This study describes the utility of Pd(II)-catalyzed C-H arylation of benzamides for constructing biaryl sulfonamides. Sulfonamides are known for their promising applications in pharmaceuticals and agrochemicals. A literature review revealed that biaryl sulfonamides were generally constructed via the traditional cross-coupling reactions. We report a progressive method for obtaining biaryl sulfonamides via the Pd(II)-catalyzed bidentate directing group (8-aminoquinoline or picolinamide)-assisted cross-coupling of sp² C-H bonds of aromatic carboxamides with iodobenzenesulfonamides. After the C-H arylation reactions, we attempted the removal of the 8-aminoquinoline from the synthesized biaryl scaffolds possessing the carboxamide and sulfonamide moieties using triflic acid. In some cases, we observed the occurrence of decarboxylation and Friedel-Crafts acylation, affording interesting aromatic scaffolds possessing the sulfonamide moiety. The current work contributes toward developing alternative ways for assembling various biaryl sulfonamides.