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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Visible-Light-Mediated Copper-Catalyzed S-Arylation of Sulfenamides with Aryl Thianthrenium Salts
Xiangyu Zhuang1, Hao Li1, Zhaoyu Feng1
1Key Laboratory of Marine Drugs, Ministry of Education; Molecular Synthesis Center, and School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, P. R. China.
Abstract:
The site-selective incorporation of sulfilimine functionalities into aromatic compounds provides a vital strategy for drug discovery in medicinal chemistry. However, green and sustainable methods for realizing the goal are still limited. Here, we report a copper-catalyzed S-arylation of sulfenamides with aryl thianthrenium salts irradiated by visible light without the photocatalyst, which exhibited fine functional-group compatibility and gave the desired products in high yields. Mechanistic investigations revealed that the key to achieving these results is the generation of an electron donor-acceptor (EDA) complex between sulfenamides and aryl thianthrenium salts under basic conditions.
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