Copper‐Catalyzed Reaction Cascade of Thiophenol Hydroxylation and S‐Arylation through Disulfide‐Directed C−H Activation. Issue 16 (9th March 2016)

• Record Type: Journal Article
• Authors: Wang, Dawei; Yu, Xin; Yao, Wei; Hu, Wenkang; Ge, Chenyang; Shi, Xiaodong
• Is Part Of: Chemistry. Volume 22:Issue 16(2016)
• Page Start: 5543
• Page End: 5546
• Publication Date: 2016-03-09
• Subjects: C−H activation -- disulfide -- homogeneous catalysis -- hydroxylation -- S-arylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600597
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Copper‐catalyzed thiophenol C−H activation is described. In 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 proceeds under mild conditions with molecular oxygen as an oxidant. Discovery of disulfide as the directing group provides a potentially new direction for catalytic C−H functionalization under mild conditions.