Pd(ii)-Catalyzed decarboxylative meta-C-H difluoromethylation

被引：32
作者：
Zhao, Huaxin [1 ]
Ma, Guobin [2 ]
Xie, Xiaojuan [1 ]
Wang, Yong [1 ]
Hao, Jian [1 ]
Wan, Wen [1 ,3 ]
机构：
[1] Shanghai Univ, Dept Chem, Shanghai, Peoples R China
[2] Shanghai Univ, Sch Sci, Shanghai, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 27期
基金：
中国国家自然科学基金;
关键词：
OXIDATIVE DECARBOXYLATION; FUNCTIONALIZATION; DIFLUOROACETATES; OLEFINATION; ACTIVATION; FLUORINE; ALKENES; PHENOL; ARENES; LIGAND;
D O I：
10.1039/c9cc00984a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A palladium(ii)-catalyzed decarboxylative meta-selective C-H difluoromethylation of arenes has been developed from easily accessible difluoroacetic acids. Initial mechanistic studies disclosed that a reasonable migratory insertion is involved in this meta-C-H functionalization.
引用
收藏
页码：3927 / 3930
页数：4
相关论文
共 54 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Palladium-Catalyzed Negishi Cross-Coupling Reaction of Aryl Halides with (Difluoromethyl)zinc Reagent [J].
Aikawa, Kohsuke ;
Serizawa, Hiroki ;
Ishii, Koki ;
Mikami, Koichi .
ORGANIC LETTERS, 2016, 18 (15) :3690-3693
[3]   Nanomolar Potency and Metabolically Stable Inhibitors of Kidney Urea Transporter UT-B [J].
Anderson, Marc O. ;
Zhang, Jicheng ;
Liu, Yan ;
Yao, Chenjuan ;
Phuan, Puay-Wah ;
Verkrnan, A. S. .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (12) :5942-5950
[4]  
Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine
[5]   MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID [J].
BLACKBURN, GM ;
ENGLAND, DA ;
KOLKMANN, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) :930-932
[6]   Organic synthesis provides opportunities to transform drug discovery [J].
Blakemore, David C. ;
Castro, Luis ;
Churcher, Ian ;
Rees, David C. ;
Thomas, Andrew W. ;
Wilson, David M. ;
Wood, Anthony .
NATURE CHEMISTRY, 2018, 10 (04) :383-394
[7]   Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C-H Bond Arylation [J].
Chen, Bo ;
Hou, Xue-Long ;
Li, Yu-Xue ;
Wu, Yun-Dong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) :7668-7671
[8]   Rhodium-Catalyzed Intermolecular C-H Silylation of Arenes with High Steric Regiocontrol [J].
Cheng, Chen ;
Hartwig, John F. .
SCIENCE, 2014, 343 (6173) :853-857
[9]   Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].
Cho, JY ;
Tse, MK ;
Holmes, D ;
Maleczka, RE ;
Smith, MR .
SCIENCE, 2002, 295 (5553) :305-308
[10]   Pd(II)-Catalyzed ortho- or meta-C-H Olefination of Phenol Derivatives [J].
Dai, Hui-Xiong ;
Li, Gang ;
Zhang, Xing-Guo ;
Stepan, Antonia F. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (20) :7567-7571
123456