Catalyst and additive-free oxidative dual C-H sulfenylation of imidazoheterocycles with elemental sulfur using DMSO as a solvent and an oxidant

被引:41
作者
Guo, Tao [1 ]
Wei, Xu-Ning [1 ]
Zhang, Miao [2 ]
Liu, Yu [1 ]
Zhu, Li-Min [1 ]
Zhao, Yun-Hui [3 ]
机构
[1] Henan Univ Technol, Sch Chem & Chem Engn, Zhengzhou 450001, Henan, Peoples R China
[2] Zhengzhou Univ, Dept Pharm, Childrens Hosp, Zhengzhou 450001, Henan, Peoples R China
[3] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Hunan, Peoples R China
关键词
ARYL; THIOLATION; CHALCOGENATION; SULFIDES; ACID; TRIFLUOROMETHYLTHIOLATION; IMIDAZOPYRIDINES; KETONES; POWDER; DIARYL;
D O I
10.1039/d0cc00043d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Dual C-H sulfenylation was used to obtain 3-vulcanized imidazoheterocycles using odorless elemental sulfur under catalyst- and additive-free conditions. C-H activation of both imidazoheterocycles and arylamines/arenols/indoles was realized by a practical protocol in which DMSO served as both a solvent and an internal oxidant.
引用
收藏
页码:5751 / 5754
页数:4
相关论文
共 60 条
[1]  
[Anonymous], SYNTHESIS
[2]   Iodine-Promoted Deoxygenative Iodization/Olefination/Sulfenylation of Ketones with Sulfonyl Hydrazides: Access to β-lodoalkenyl Sulfides [J].
Bao, Yishu ;
Yang, Xiuqin ;
Zhou, Qingfa ;
Yang, Fulai .
ORGANIC LETTERS, 2018, 20 (07) :1966-1969
[3]   NH4I-catalyzed chalcogen(S/Se)-functionalization of 5-membered N-heteroaryls under metal-free conditions [J].
Bettanin, Luana ;
Saba, Sumbal ;
Doerner, Carlos, V ;
Franco, Marcelo S. ;
Godoi, Marcelo ;
Rafique, Jamal ;
Braga, Antonio L. .
TETRAHEDRON, 2018, 74 (29) :3971-3980
[4]   Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF3SiMe3 and Elemental Sulfur [J].
Chen, Chao ;
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12454-12457
[5]   External Oxidant-Free Regioselective Cross Dehydrogenative Coupling of 2-Arylimidazoheterocycles and Azoles with H2 Evolution via Photoredox Catalysis [J].
Chen, Hong ;
Yi, Hong ;
Tang, Zilu ;
Bian, Changliang ;
Zhang, Heng ;
Lei, Aiwen .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (17) :3220-3227
[6]   Graphene oxide mediated thiolation of indoles in water: a green and sustainable approach to synthesize 3-sulfenylindoles [J].
Chen, Min ;
Luo, Yi ;
Zhang, Chen ;
Guo, Li ;
Wang, Qiantao ;
Wu, Yong .
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (01) :116-120
[7]   Sulfite-Promoted Synthesis of N-Difluoromethylthioureas via the Reaction of Azoles with Bromodifluoroacetate and Elemental Sulfur [J].
Deng, Jian-Chao ;
Gao, Yong-Chao ;
Zhu, Zhu ;
Xu, Li ;
Li, Zhao-Dong ;
Tang, Ri-Yuan .
ORGANIC LETTERS, 2019, 21 (02) :545-548
[8]   Catalytic, Enantioselective Sulfenylation of Ketone-Derived Enoxysilanes [J].
Denmark, Scott E. ;
Rossi, Sergio ;
Webster, Matthew P. ;
Wang, Hao .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (37) :13016-13028
[9]   Synergistic Dual Role of [hmim]Br-ArSO2Cl in Cascade Sulfenylation-Halogenation of Indole: Mechanistic Insight into Regioselective C-S and C-S/C-X (X = Cl and Br) Bond Formation in One Pot [J].
Equbal, Danish ;
Singh, Richa ;
Saima ;
Lavekar, Aditya G. ;
Sinha, Arun K. .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (05) :2660-2675
[10]   Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides [J].
Fang, Yi ;
Rogge, Torben ;
Ackermann, Lutz ;
Wang, Shun-Yi ;
Ji, Shun-Jun .
NATURE COMMUNICATIONS, 2018, 9