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Ni‐Catalyzed Synthesis of Fluoroarenes via [2+2+2] Cycloaddition Involving α‐Fluorine Elimination
Author(s) -
Fujita Takeshi,
Watabe Yota,
Ichitsuka Tomohiro,
Ichikawa Junji
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201502744
Subject(s) - cycloaddition , catalysis , chemistry , nickel , fluoride , molecule , fluorine , catalytic cycle , boron , photochemistry , medicinal chemistry , organic chemistry , inorganic chemistry
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.