title: Copper-Catalyzed Reaction Cascade of Thiophenol Hydroxylation and S-Arylation through Disulfide-Directed C-H Activation.
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.
authors.affiliation: The 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.
authors.forename: Dawei
authors.initials: D
authors.lastname: Wang
authors.affiliation: The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, China.
authors.forename: Xin
authors.initials: X
authors.lastname: Yu
authors.affiliation: The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Yao
authors.affiliation: The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, China.
authors.forename: Wenkang
authors.initials: W
authors.lastname: Hu
authors.affiliation: The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, 214122, China.
authors.forename: Chenyang
authors.initials: C
authors.lastname: Ge
authors.affiliation: Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA. xmshi@usf.edu.
authors.forename: Xiaodong
authors.initials: X
authors.lastname: Shi
keywords: C−H activation; S-arylation; disulfide; homogeneous catalysis; hydroxylation