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Biomolecule-Compatible Dehydrogenative Chan-Lam Coupling of Free Sulfilimines

Tingting Meng, Lucille A. Wells, Tianxin Wang, Jinyu Wang, Shishuo Zhang, Jie Wang, Marisa C. Kozlowski* and Tiezheng Jia*

*UPenn, 231 South 34th Street, Philadelphia, Pennsylvania 19104, USA; SUSTech, 1088 Xueyuan Blvd., Shenzhen, Guangdong 518055, China, Email: marisasas.upenn.edu, jiatzsustech.edu.cn

T. Meng, L. A. Wells, T. Wang, J. Wang, S. Zhang, J. Wang, M. C. Kozlowski, T. Jia, J. Am. Chem. Soc., 2022, 144, 12476-12487.

DOI: 10.1021/jacs.2c04627



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Abstract

A terminal oxidant-free copper-catalyzed dehydrogenative Chan-Lam coupling of free diaryl sulfilimines with arylboronic acids offers excellent chemoselectivity and broad substrate compatibility. This protocol is suitable for late-stage functionalization of complex peptides.

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proposed reaction pathway



Copper-Catalyzed Chan-Lam Coupling of NH-Diaryl Sulfilimines with Arylboronic Acids

To an oven-dried microwave vial equipped with a stir bar was added free sulfilimine (0.3 mmol, 1.0 equiv), boronic acid (0.45 mmol, 1.5 equiv), CuBr (2.2 mg, 0.015 mmol, 5 mol %) under an argon atmosphere in a dry box. The vial was capped with a septum and removed from the dry box. iPrOH (3.0 mL) was added into the reaction vial via syringe, and the reaction solution was stirred at room temperature under argon atmosphere for 24 h. Upon completion of the reaction, the vial was opened to air, and the reaction mixture was passed through a short pad of silica gel. The pad was then rinsed with 20:1 dichloromethane:methanol (20.0 mL). The solvent was removed under reduced pressure. The residue was purified by flash chromatography to afford the desired product.


Key Words

sulfilimines, Chan-Lam coupling


ID: J48-Y2022