China's flourishing synthetic organofluorine chemistry: innovations in the new millennium

被引:153
作者
Liu, Qinghe [1 ]
Ni, Chuanfa [1 ]
Hu, Jinbo [1 ]
机构
[1] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
fluorine; organic chemistry; synthetic methods; fluorination; trifluoromethylation; trifluoromethylthiolation; difluoromethylation; difluoroalkylation; fluoromethylation; fluoroolefination; C-F BOND; COPPER-CATALYZED TRIFLUOROMETHYLATION; ARYL BORONIC ACIDS; ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; MEDIATED OXIDATIVE TRIFLUOROMETHYLATION; HIGHLY ENANTIOSELECTIVE CONSTRUCTION; ELECTRON-DEFICIENT POLYFLUOROARENES; CARBON-FLUORINE BOND; ALPHA-DIAZO ESTERS; ONE-POT SYNTHESIS;
D O I
10.1093/nsr/nwx058
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
The new millennium has witnessed the rapid development of synthetic organofluorine chemistry all over the world, and chemists in China have made significant contributions in this field. This review aims to provide a brief introduction to China's primary innovations from 2000 to early 2017, covering fluorination, fluoroalkylation, fluoromethylthiolation, fluoroolefination and polyfluoroarylation, as well as synthesis with fluorinated building blocks. Recent advances in the chemistry of difluorocarbene and the chemistry of carbon-fluorine bond activation are also discussed. As a conclusion, the review ends with some personal perspectives on the future development of China's synthetic organofluorine chemistry.
引用
收藏
页码:303 / 325
页数:23
相关论文
共 274 条
[41]   A General Synthesis of Fluoroalkylated Alkenes by Palladium-Catalyzed Heck-Type Reaction of Fluoroalkyl Bromides [J].
Feng, Zhang ;
Min, Qiao-Qiao ;
Zhao, Hai-Yang ;
Gu, Ji-Wei ;
Zhang, Xingang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) :1270-1274
[42]   Palladium-Catalyzed Difluoroalkylation of Aryl Boronic Acids: A New Method for the Synthesis of Aryldifluoromethylated Phosphonates and Carboxylic Acid Derivatives [J].
Feng, Zhang ;
Min, Qiao-Qiao ;
Xiao, Yu-Lan ;
Zhang, Bo ;
Zhang, Xingang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (06) :1669-1673
[43]   AgF-Mediated Fluorinative Cross-Coupling of Two Olefins: Facile Access to α-CF3 Alkenes and β-CF3 Ketones [J].
Gao, Bing ;
Zhao, Yanchuan ;
Hu, Jinbo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) :638-642
[44]   AgF-Mediated Fluorinative Homocoupling of gem-Difluoroalkenes [J].
Gao, Bing ;
Zhao, Yanchuan ;
Ni, Chuanfa ;
Hu, Jinbo .
ORGANIC LETTERS, 2014, 16 (01) :102-105
[45]   Highly Enantioselective Construction of Trifluoromethylated All-Carbon Quaternary Stereocenters via Nickel-Catalyzed Friedel-Crafts Alkylation Reaction [J].
Gao, Jian-Rong ;
Wu, Hao ;
Xiang, Bin ;
Yu, Wu-Bin ;
Han, Liang ;
Jia, Yi-Xia .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (08) :2983-2986
[46]   Synthesis of diaryldifluoromethanes by Pd-catalyzed difluoroalkylation of arylboronic acids [J].
Gu, Ji-Wei ;
Guo, Wen-Hao ;
Zhang, Xingang .
Organic Chemistry Frontiers, 2015, 2 (01) :38-41
[47]   Cooperative dual palladium/silver catalyst for direct difluoromethylation of aryl bromides and iodides [J].
Gu, Yang ;
Leng, Xuebing ;
Shen, Qilong .
NATURE COMMUNICATIONS, 2014, 5
[48]   Visible-Light-Induced Radical Tandem Aryldifluoroacetylation of Cinnamamides: Access to Difluoroacetylated Quinolone-2-ones And 1-Azaspiro[4.5]decanes [J].
Gu, Zhangxi ;
Zhang, Honglin ;
Xu, Pan ;
Cheng, Yixiang ;
Zhu, Chengjian .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (14-15) :3057-3063
[49]   TfNHNHBoc as a Trifluoromethylating Agent for Vicinal Difunctionalization of Terminal Alkenes [J].
Guo, Jing-Yu ;
Wu, Ruo-Xin ;
Jin, Ji-Kang ;
Tian, Shi-Kai .
ORGANIC LETTERS, 2016, 18 (15) :3850-3853
[50]  
Guo S, 2017, NAT CHEM, V9, P546, DOI [10.1038/NCHEM.2711, 10.1038/nchem.2711]