Functionalization of Sulfonamide-Containing Peptides through Late-Stage Palladium-Catalyzed C(sp3)–H Arylation

• DOI: 10.1021/acs.orglett.9b01953
• Publication Date: 2019-07-16T18:14:07Z
• Authors: Qingqing Bai; Jian Tang; Huan Wang
• Keywords: Sulfonamides; Amino Acids; Peptides; 01 natural sciences; Catalysis; Palladium; 3. Good health; 0104 chemical sciences

Bioactive peptides are emerging as promising candidates of clinic therapeutics. Here, we report a method for late-stage functionalization of sulfonamide-containing peptides through Pd-catalyzed C(sp3)-H arylation. In this protocol, the backbones of N-sulfonated peptides act as directing groups, which allows site-specific arylation of benzylsulfonamide moiety. This chemistry exhibits broad substrate scope and can be utilized to synthesize peptide-peptide and peptide-amino acid conjugates. Our results highlight the potency of the backbone of peptidomimetics in promoting Pd-catalyzed functionalization.