18232-05-8Relevant academic research and scientific papers
Copper-Catalyzed Reaction Cascade of Thiophenol Hydroxylation and S-Arylation through Disulfide-Directed C-H Activation
Wang, Dawei,Yu, Xin,Yao, Wei,Hu, Wenkang,Ge, Chenyang,Shi, Xiaodong
, p. 5543 - 5546 (2016)
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.
Oxidative radical coupling of hydroquinones and thiols using chromic acid: One-pot synthesis of quinonyl alkyl/aryl thioethers
Adarsh Krishna, T. P.,Chinnasamy, Suresh,Ilangovan, Andivelu,Pandaram, Sakthivel
, p. 19454 - 19462 (2020/06/04)
An efficient, simple and practical protocol for one-pot sequential oxidative radical C-H/S-H cross-coupling of thiols with hydroquinones (HQs) and oxidation leading to the formation of quinonyl alkyl/aryl thioethers using H2CrO4was developed. This cross-coupling of thiyl and aryl radicals offers mono thioethers in good to moderate yield and works well with a wide variety of thiols. Similarly, this method works well for coupling of 2-amino thiophenol and HQs to form phenothiazine-3-ones5a-c. C-S bond formationviathioether synthesis was observed using a chromium reagent for the first time. Theoretical studies on the pharmacokinetic properties of compounds5a-crevealed that due to drug-like properties, compound5bstrongly binds with Alzheimer's disease (AD) associated AChE target sites.
The convenient synthesis and reaction of 2-(arylthio)phenols under ligand-free conditions: arylthioquinone preparation through cascade C–H functionalization and oxidation from arylthiols and aryl iodides
Wang, Dawei,Yu, Xiaoli,Wang, Likui,Yao, Wei,Xu, Zhaojun,Wan, Huida
supporting information, p. 5211 - 5214 (2016/11/13)
A convenient and simple method for copper-catalyzed synthesis of 2-(arylthio)phenols through C–H functionalization of arylthiols and aryl iodides was developed under ligand-free conditions without nitrogen protection. In addition, arylthioquinone derivatives were very easily prepared for one more step of oxidation with moderate to good yields. This provide an alternative and efficient way to 2-(arylthio)phenols and arylthioquinone derivatives smoothly without using ligands and nitrogen protection or expensive arylboronic acids.
