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Functionalization of Sulfonamide-Containing Peptides through Late-Stage Palladium-Catalyzed C(sp3)-H Arylation
Qingqing Bai1, Jian Tang2, Huan Wang1
1State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering , Nanjing University , Nanjing 210093 , China.
Abstract:
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.
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