Work

Construction of Biaryl Sulfonamides via Pd(II)-Catalyzed Cross-Coupling of C(sp 2 )-H Bonds with Iodobenzenesulfonamides

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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 sp 2 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.

Source: ACS Omega

DOI: 10.1021/acsomega.4c10558

Authors: Debabrata Bhattacharya, Sampurna Pal, Indranil Banerjee, Srinivasarao Arulananda Babu

Institution: Indian Institute of Science Education and Research Mohali

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,935

Funders: Department of Science and Technology, Ministry of Science and Technology, India, Indian Institute of Science Education and Research Mohali