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Published on: April 9, 2018
Copper-Catalyzed Reaction Cascade of Thiophenol Hydroxylation and S-Arylation through Disulfide-Directed C-H
Dawei Wang1, Xin Yu2, Wei Yao2
1The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, China. wangdw@jiangnan.edu.cn.
Abstract:
Copper-catalyzed thiophenol C-H activation is described. Through an initial attempt to conduct C-arylation with arylboronic acid, a rather surprising sequential C-H activation and S-arylation was discovered. Mechanistic investigation revealed the disulfide intermediate as the key component in directing C-H oxidation. The overall reaction proceeded under mild conditions with molecular oxygen as the oxidant. Discovery of disulfide as the directing group provides a potential new direction for catalytic C-H functionalization under mild conditions.
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