1254831-75-8Relevant academic research and scientific papers
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
, p. 5211 - 5214 (2016)
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.
Metal–organic frameworks of Cu2(TPTC)-catalyzed cascade C–S coupling/Csp2–H hydroxylation reaction
Tian, An-Qi,Liu, Shan,Ren, Zhi-Lin,Wang, Long,Li, Dong-Sheng
, p. 1339 - 1345 (2020/01/31)
Abstract: This paper reports a novel disulfide-directed Csp2–H hydroxylation cascade reaction strategy catalyzed by Cu2(TPTC), a metal–organic framework material with binuclear Cu(II) paddlewheel nodes. In the strategy, Cu2(TPTC) MOF can effectively catalyze the coupling reaction of disulfide and arylboronic acid, and realize the disulfide-directed Csp2–H hydroxylation reaction. This reaction proceeded well under Cu2(TPTC) MOF catalyst with good yields, which provides an efficient method to the synthesis of functional organic molecules, such as 2-(phenylthio)phenols derivatives. Graphic abstract: [Figure not available: see fulltext.].
Disulfide-Directed C–H Hydroxylation for Synthesis of Sulfonyl Diphenyl Sulfides and 2-(Phenylthio)phenols with Oxygen as Oxidant
Wang, Long,Xie, Yi-Bi,Huang, Nian-Yu,Zhang, Nuo-Nuo,Li, De-Jiang,Hu, Yu-Lin,Liu, Ming-Guo,Li, Dong-Sheng
, p. 779 - 785 (2017/03/11)
Compared to N, O and P as directing functional atoms, the application of directing group containing sulfur atoms for transition metal-catalyzed C–H activation is much more difficult for the known reason (some metal catalysts are easily poisoned by sulfur). Here, the disulfide-directed C–H activation for thew synthesis of sulfonyl diphenyl sulfides was realized for the first time by a copper-catalyzed, tandem, one-step C–S coupling/hydroxylation of disulfides and arylboronic acids with oxygen as the oxidant. This method provides a mild and easy method for the synthesis of sulfonyl diphenyl sulfides and 2-(phenylthio)phenol derivatives and avoids producing sulfoxides and sulfones under air conditions and elevated temperatures. (Figure presented.).
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
supporting information, p. 5543 - 5546 (2016/04/20)
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.
