Visible light mediated C-H trifluoromethylation of (hetero)arenes

被引:18
作者
Xiao, Fang [1 ,2 ]
Jin-Hong Lin [2 ,3 ]
Hao, Fei [2 ,4 ]
Zheng, Xing [1 ]
Guo, Yu [1 ]
Ji-Chang Xiao [2 ]
机构
[1] Univ South China, Inst Pharm & Pharmacol, Hunan Prov Key Lab Tumor Microenvironm Respons Dr, Hengyang 421001, Peoples R China
[2] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[3] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China
[4] Qilu Univ Technol, Shandong Acad Sci, Shandong Prov Key Lab Mol Engn, Jinan 250353, Peoples R China
关键词
PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; CATALYZED TRIFLUOROMETHYLATION; AROMATIC-COMPOUNDS; ARENES; FLUORINE; PERFLUOROALKYLATION; HETEROARENES;
D O I
10.1039/d2qo00067a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A protocol for visible light mediated C-H trifluoromethylation of unactivated (hetero)arenes under blue LED irradiation has been developed. The reaction enables the rapid construction of a range of CF3-containing (hetero)arenes in moderate to high yields from the readily accessible trifluoromethylsulfonyl-pyridinium salt (TFSP). This protocol is also suitable for nitrogen-containing aromatic heterocycles, which are potentially useful in medicinal chemistry.
引用
收藏
页码:1982 / 1985
页数:4
相关论文
共 50 条
[21]   Catalyst-free direct C-H trifluoromethylation of arenes in water-acetonitrile [J].
Wang, Dangui ;
Deng, Guo-Jun ;
Chen, Shiya ;
Gong, Hang .
GREEN CHEMISTRY, 2016, 18 (22) :5967-5970
[22]   Mechanistic study of visible light-driven CdS or g-C3N4-catalyzed C-H direct trifluoromethylation of (hetero)arenes using CF3SO2Na as the trifluoromethyl source [J].
Wang, Lele ;
Liu, Ming ;
Zha, Wenying ;
Wei, Yingcong ;
Ma, Xiongfeng ;
Xu, Chunwang ;
Lu, Chenggang ;
Qin, Nanfang ;
Gao, Li ;
Qiu, Wenzhao ;
Sa, Rongjian ;
Fu, Xianzhi ;
Yuan, Rusheng .
JOURNAL OF CATALYSIS, 2020, 389 :533-543
[23]   A general and practical Ni-catalyzed C-H perfluoroalkylation of (hetero)arenes [J].
Zhang, Shaoke ;
Rotta-Loria, Nicolas ;
Weniger, Florian ;
Rabeah, Jabor ;
Neumann, Helfried ;
Taeschler, Christoph ;
Beller, Matthias .
CHEMICAL COMMUNICATIONS, 2019, 55 (47) :6723-6726
[24]   Metal-Catalyzed/Mediated Aromatic C-H Bond Trifluoromethylation [J].
Kamei, Toshiyuki .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2012, 70 (07) :756-757
[25]   Silver-Catalyzed C-H Trifluoromethylation of Arenes Using Trifluoroacetic Acid as the Trifluoromethylating Reagent [J].
Shi, Guangfa ;
Shao, Changdong ;
Pan, Shulei ;
Yu, Jingxun ;
Zhang, Yanghui .
ORGANIC LETTERS, 2015, 17 (01) :38-41
[26]   Metal-Free, Visible-Light-Mediated Direct C-H Trifluoromethylation of Hydrazones with NADH Coenzyme Model Catalyst [J].
Huang, Bei ;
Bu, Xiao-Song ;
Xu, Jun ;
Dai, Jian-Jun ;
Feng, Yi-Si ;
Xu, Hua-Jian .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (01) :137-140
[27]   Recent Developments on the Trifluoromethylation of (Hetero)Arenes [J].
Wu, Xiao-Feng ;
Neumann, Helfried ;
Beller, Matthias .
CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (08) :1744-1754
[28]   Oxidative C-H/C-H Coupling Reactions between Two (Hetero)arenes [J].
Yang, Yudong ;
Lan, Jingbo ;
You, Jingsong .
CHEMICAL REVIEWS, 2017, 117 (13) :8787-8863
[29]   Cu(II)-Mediated Ortho C-H Alkynylation of (Hetero)Arenes with Terminal Alkynes [J].
Shang, Ming ;
Wang, Hong-Li ;
Sun, Shang-Zheng ;
Dai, Hui-Xiong ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (33) :11590-11593
[30]   Visible-light-mediated direct perfluoroalkylation and trifluoromethylation of free anilines [J].
He, Chun-Yang ;
Gu, Ji-Wei ;
Zhang, Xingang .
TETRAHEDRON LETTERS, 2017, 58 (41) :3939-3941