biostudies-literatureMeng TShenzhen Nobel Prize Scientists Laboratory ProjectGuangdong-Joint Foundation of ShenzhenNatural Science Foundation of Guangdong ProvinceGuangdong Provincial Key Laboratory Of CatalysisNational Institute of General Medical SciencesNIGMS NIH HHS12476-12487https://www.ebi.ac.uk/biostudies/studies/S-EPMC9588409biostudies-literatureUnknown144(27)Inspired by the discovery of a S═N bond in the collagen IV network and its essential role in stabilizing basement membranes, sulfilimines have drawn much attention in the fields of chemistry and biology. However, their further uptake is hindered by the lack of mild, efficient, and environmentally benign protocols by which sulfilimines can be constructed under biomolecule-compatible conditions. Here, we report a terminal oxidant-free copper-catalyzed dehydrogenative Chan-Lam coupling of free diaryl sulfilimines with arylboronic acids with excellent chemoselectivity and broad substrate compatibility. The mild reaction conditions and biomolecule-compatible nature allow the employment of this protocol in the late-stage functionalization of complex peptides, and more importantly, as an effectivJournal of the American Chemical SocietyBiomolecule-Compatible Dehydrogenative Chan-Lam Coupling of Free Sulfilimines.PMC95884092021B15151200462022A15150117702020B121201002R35 GM131902C17783101Meng TJia TWang TZhang SWells LAWang JKozlowski MCfalseBiomolecule-Compatible Dehydrogenative Chan-Lam Coupling of Free Sulfilimines.Inspired by the discovery of a S═N bond in the collagen IV network and its essential role in stabilizing basement membranes, sulfilimines have drawn much attention in the fields of chemistry and biology. However, their further uptake is hindered by the lack of mild, efficient, and environmentally benign protocols by which sulfilimines can be constructed under biomolecule-compatible conditions. Here, we report a terminal oxidant-free copper-catalyzed dehydrogenative Chan-Lam coupling of free diaryl sulfilimines with arylboronic acids with excellent chemoselectivity and broad substrate compatibility. The mild reaction conditions and biomolecule-compatible nature allow the employment of this protocol in the late-stage functionalization of complex peptides, and more importantly, as an effectiv2022-01-01T00:00:00Z2022 Jul2025-04-26T15:12:06.852Z2025-04-06T14:51:30.516ZS-EPMC95884093576772710.1021/jacs.2c04627