Ni-Catalyzed Synthesis of Fluoroarenes via [2+2+2] Cycloaddition Involving α-Fluorine Elimination.
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 C-F and C-H bonds in difluoroethylene. The catalytic cycle is established by reduction of the intermediary Ni(II) fluoride with a triethylborane-based borate.
Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571 (Japan).
Takeshi
T
Fujita
Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571 (Japan).
Yota
Y
Watabe
Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571 (Japan).
Tomohiro
T
Ichitsuka
Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571 (Japan). junji@chem.tsukuba.ac.jp.
Junji
J
Ichikawa
CF bond activation; alkynes; fluoroalkenes; fluoroarenes; nickel