Recent Advances and Perspectives of Transition Metal-Catalyzed Asymmetric Fluorination Reactions

被引:40
作者
Chen, Chaohuang [1 ]
Fu, Liang [1 ]
Chen, Pinhong [1 ]
Liu, Guosheng [1 ]
机构
[1] Univ Chinese Acad Sci, Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
关键词
metal-catalyzed; asymmetric; fluorination; trifluoromethylthiolation; trifluoromethoxylation; C-H FLUORINATION; ENANTIOSELECTIVE FLUORINATION; OXIDATIVE AMINOFLUORINATION; ELECTROPHILIC FLUORINATION; REDUCTIVE ELIMINATION; ALLYLIC FLUORINATION; BOND FORMATION; PALLADIUM; TRIFLUOROMETHYLATION; TRIFLUOROMETHOXYLATION;
D O I
10.1002/cjoc.201700489
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of fluorine-containing molecules has received intensive attention in recent years due to the great value of fluorides, however, the transition metal-catalyzed asymmetric construction of CF bonds is much less developed. This review presents the recent advancement of transition metal-catalyzed asymmetric fluorination reactions, in which the final CF bond is from reductive elimination of organometallic complexes. In addition, the perspective of the field is also provided for the future studies of asymmetric fluorinations and the related transformations, such as trifluoromethylation, trifluoromethylthiolation and trifluoromethoxylation.
引用
收藏
页码:1781 / 1788
页数:8
相关论文
共 75 条
[1]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[2]   Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex [J].
Ball, Nicholas D. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :3796-+
[3]   Catalytic, Diastereoselective 1,2-Difluorination of Alkenes [J].
Banik, Steven M. ;
Medley, Jonathan William ;
Jacobsen, Eric N. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (15) :5000-5003
[4]   New entries toward the synthesis of OCF3-containing molecules [J].
Besset, Tatiana ;
Jubault, Philippe ;
Pannecoucke, Xavier ;
Poisson, Thomas .
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (08) :1004-1010
[5]   Recent Progress in Asymmetric Fluorination and Trifluoromethylation Reactions [J].
Bizet, Vincent ;
Besset, Tatiana ;
Ma, Jun-An ;
Cahard, Dominique .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2014, 14 (07) :901-940
[6]   Palladium-Catalyzed Allylic C-H Fluorination [J].
Braun, Marie-Gabrielle ;
Doyle, Abigail G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) :12990-12993
[7]   Palladium(II)-Catalyzed Selective Monofluorination of Benzoic Acids Using a Practical Auxiliary: A Weak-Coordination Approach [J].
Chan, Kelvin S. L. ;
Wasa, Masayuki ;
Wang, Xisheng ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9081-9084
[8]   Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].
Charpentier, Julie ;
Frueh, Natalja ;
Togni, Antonio .
CHEMICAL REVIEWS, 2015, 115 (02) :650-682
[9]   Recent Advances in Radical Fluorination [J].
Chatalova-Sazepin, Claire ;
Hemelaere, Remy ;
Paquin, Jean-Francois ;
Sammis, Glenn M. .
SYNTHESIS-STUTTGART, 2015, 47 (17) :2554-2569
[10]   Palladium-Catalyzed Intramolecular Aminotrifluoromethoxylation of Alkenes [J].
Chen, Chaohuang ;
Chen, Pinhong ;
Liu, Guosheng .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) :15648-15651