Ni-Catalyzed Synthesis of Fluoroarenes via [2+2+2] Cycloaddition Involving -Fluorine Elimination

被引:22
作者
Fujita, Takeshi [1 ]
Watabe, Yota [1 ]
Ichitsuka, Tomohiro [1 ]
Ichikawa, Junji [1 ]
机构
[1] Univ Tsukuba, Fac Pure & Appl Sci, Div Chem, Tsukuba, Ibaraki 3058571, Japan
关键词
alkynes; CF bond activation; fluoroalkenes; fluoroarenes; nickel; DIFLUORO-SUBSTITUTED 1,6-ENYNES; F BOND ACTIVATION; ARYL FLUORIDES; COUPLING REACTIONS; VINYLIC FLUORINES; LATE-STAGE; ALKYNES; CYCLIZATION; PALLADIUM; ARYNES;
D O I
10.1002/chem.201502744
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A method for direct synthesis of tetrasubstituted fluoroarenes via nickel-catalyzed [2+2+2] cycloaddition is presented. The reaction combines one molecule of 1,1-difluoroethylene with two molecules of alkynes and involves sequential cleavage of the CF and CH bonds in difluoroethylene. The catalytic cycle is established by reduction of the intermediary Ni-II fluoride with a triethylborane-based borate.
引用
收藏
页码:13225 / 13228
页数:4
相关论文
共 63 条
[1]   Nucleophilic routes to selectively fluorinated aromatics [J].
Adams, DJ ;
Clark, JH .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (04) :225-231
[2]  
Anbarasan P., 2010, ANGEW CHEM, V122, P2265
[3]   Efficient Synthesis of Aryl Fluorides [J].
Anbarasan, Pazhamalai ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) :2219-2222
[4]   Late-stage [18F]fluorination: new solutions to old problems [J].
Brooks, Allen F. ;
Topczewski, Joseph J. ;
Ichiishi, Naoko ;
Sanford, Melanie S. ;
Scott, Peter J. H. .
CHEMICAL SCIENCE, 2014, 5 (12) :4545-4553
[5]   Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [J].
Campbell, Michael G. ;
Ritter, Tobias .
CHEMICAL REVIEWS, 2015, 115 (02) :612-633
[6]   Metal-free electrophilic fluorination of alkyl trifluoroborates and boronic acids [J].
Cazorla, Clement ;
Metay, Estelle ;
Andrioletti, Bruno ;
Lemaire, Marc .
TETRAHEDRON LETTERS, 2009, 50 (27) :3936-3938
[7]   Understanding the regioselectivity in Scholl reactions for the synthesis of oligoarenes [J].
Danz, Michael ;
Tonner, Ralf ;
Hilt, Gerhard .
CHEMICAL COMMUNICATIONS, 2012, 48 (03) :377-379
[8]   Recent advances in [2+2+2] cycloaddition reactions [J].
Dominguez, Gema ;
Perez-Castells, Javier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3430-3444
[9]   Pinpoint-Fluorinated Phenacenes: New Synthesis and Solubility Enhancement Strategies [J].
Fuchibe, Kohei ;
Morikawa, Toshiyuki ;
Shigeno, Kento ;
Fujita, Takeshi ;
Ichikawa, Junji .
ORGANIC LETTERS, 2015, 17 (05) :1126-1129
[10]   Vinylic C-F bond activation with low-valent zirconocene: the generation and cross-coupling reactions of 1-fluorovinylzirconocene [J].
Fujiwara, M ;
Ichikawa, J ;
Okauchi, T ;
Minami, T .
TETRAHEDRON LETTERS, 1999, 40 (40) :7261-7265