Palladium-Catalyzed C-F Bond Formation via Directed C-H Activation

被引:77
作者
Li, Yan [1 ]
Wu, Yun [1 ]
Li, Guang-Shui [1 ]
Wang, Xi-Sheng [1 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
关键词
catalysis; C-F bond formation; C-H activation; fluorination; palladium; REDUCTIVE ELIMINATION; MEDICINAL CHEMISTRY; ORTHO-FLUORINATION; FUNCTIONALIZATION; RHODIUM; MECHANISM; PHARMACEUTICALS; CONVERSION; COMPLEXES; ARYLATION;
D O I
10.1002/adsc.201400101
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Palladium-catalyzed CF bond formation via directed CH activation has recently emerged as a significant method to introduce fluorine atoms into organic molecules in an atom- and step-economical path. At the interface between fluorine chemistry and synthetic organic chemistry, the development of direct fluorinations of the CH bond remains sluggish, due to the major challenge of reductive elimination to afford the CF bond. One strategy is to oxidize palladium(II) species to more electron-deficient palladium(IV or III) fluorides to promote the CF bond forming reductive elimination, which opens up palladium-catalyzed CH fluorination as a powerful transformation. This focused review gives a brief summary of the mere handful of examples, including C(sp(2))F and C(sp(3))F bond formations, in this field so far.
引用
收藏
页码:1412 / 1418
页数:7
相关论文
共 125 条
[1]   Palladium-mediated intramolecular biaryl coupling reaction for natural product synthesis [J].
Abe, Hitoshi ;
Harayama, Takashi .
HETEROCYCLES, 2008, 75 (06) :1305-1320
[2]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[3]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[4]   Nucleophilic routes to selectively fluorinated aromatics [J].
Adams, DJ ;
Clark, JH .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (04) :225-231
[5]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[6]   Metal-Free Fluorination of C(sp3)-H Bonds Using a Catalytic N-Oxyl Radical [J].
Amaoka, Yuuki ;
Nagatomo, Masanori ;
Inoue, Masayuki .
ORGANIC LETTERS, 2013, 15 (09) :2160-2163
[7]   Molecular imaging with PET [J].
Ametamey, Simon M. ;
Honer, Michael ;
Schubiger, Pius August .
CHEMICAL REVIEWS, 2008, 108 (05) :1501-1516
[8]  
[Anonymous], 2012, ANGEW CHEM INT ED, V51, P3414
[9]  
[Anonymous], 2009, ANGEW CHEM INT ED
[10]  
[Anonymous], 2011, ANGEW CHEM INT ED, V50, P9081