Premium
CF Activation in Perfluorinated Arenes with Isonitriles under UV‐Light Irradiation
Author(s) -
Dewanji Abhishek,
MückLichtenfeld Christian,
Bergander Klaus,
Daniliuc Constantin G.,
Studer Armido
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.201502298
Subject(s) - chemistry , regioselectivity , alkyl , aryl , fluorine , irradiation , medicinal chemistry , photochemistry , reaction mechanism , organic chemistry , catalysis , physics , nuclear physics
Due to the great value of fluorinated arenes in agrochemistry, medicinal chemistry and materials science, development of methods for preparation of fluorinated arenes is of high importance. They can be either accessed by arene fluorination or by partial arene defluorination. However, the carbonfluorine bond belongs to the strongest σ‐bonds, which renders CF activation highly challenging. Here it is shown that aryl and alkyl isonitriles efficiently activate the strong CF bond in perfluoroarenes by simple UV irradiation under mild conditions. Reactions proceed by formal direct insertion of the isonitrile into the CF bond without any transition metal. Activation occurs at arene CF bonds whereas aliphatic CF bonds remain unreacted. For selected perfluoroarenes CF activation occurs with high regioselectivity and resulting imidoyl fluorides are transformed into other valuable compounds. Theoretical studies give insights into the reaction mechanism.