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 catalyti...

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Bibliographic Details
Published in:Chemistry : a European journal 2015-09, Vol.21 (38), p.13225-13228
Main Authors: Fujita, Takeshi, Watabe, Yota, Ichitsuka, Tomohiro, Ichikawa, Junji
Format: Article
Language:English
Subjects:
Alkynes
Borates
Catalysis
Cleavage
Cycloaddition
CF bond activation
Fluorides
fluoroalkenes
fluoroarenes
Nickel
Synthesis
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Summary: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 NiII fluoride with a triethylborane‐based borate. A method for direct synthesis of tetrasubstituted fluoroarenes by 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 intermediate NiII fluoride with a triethylborane‐based borate.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201502744