Citation: Er-Meng Wang, Ziyi Wang, Xu Ban, Xiaowei Zhao, Yanli Yin, Zhiyong Jiang. Chemoselective photocatalytic sulfenylamination of alkenes with sulfenamides via energy transfer[J]. Chinese Chemical Letters, ;2024, 35(12): 109843. doi: 10.1016/j.cclet.2024.109843 shu

Chemoselective photocatalytic sulfenylamination of alkenes with sulfenamides via energy transfer

Er-Meng Wang ^{a, 1} ,
Ziyi Wang ^{a, 1} ,
Xu Ban ^b ,
Xiaowei Zhao ^a ,
Yanli Yin ^{b, c, *,} ,
Zhiyong Jiang ^{a, b, *,}

a.
Henan Key Laboratory of Natural Medicine Innovation and Transformation, Henan University, Kaifeng 475004, China
b.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China
c.
College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, China

2019142@htu.edu.cn

chmjzy@henu.edu.cn

jiangzhiyong@htu.edu.cn

Received Date: 25 December 2023
Revised Date: 19 March 2024
Accepted Date: 29 March 2024
Available Online: 29 March 2024

Figures(6)

β-Amino sulfides hold significant biological importance, motivating the development of several methods for sulfenylamination of alkenes. However, these methods often involve a three-component system with limited alkene substrate range. In this study, we present a pioneering two-component approach utilizing readily accessible sulfenamides as efficient difunctionalization reagents. Key to its success is the careful selection of a suitable photosensitizer, which enables precise modulation of sulfenamides by promoting unprecedented energy transfer rather than traditional single-electron oxidation. This novel strategy leads to the concurrent formation of N- and S-radical species, ensuring high regioselectivity for both electron-neutral and electron-deficient alkenes. As a result, a wide range of valuable β-amino sulfides, including those with congested amine groups, can be readily synthesized. These findings highlight the potential of this method for the efficient synthesis of diverse functionalized β-amino sulfides.
- Photocatalysis,
- Energy transfer,
- Sulfenamides,
- Sulfenylamination,
- Alkenes
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