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Dewanji A, Mück-Lichtenfeld C, Bergander K, et al. C-F Activation in Perfluorinated Arenes with Isonitriles under UV-Light Irradiation. Chemistry. 2015;21(35):12295-8doi: 10.1002/chem.201502298.
Dewanji, A., Mück-Lichtenfeld, C., Bergander, K., Daniliuc, C. G., & Studer, A. (2015). C-F Activation in Perfluorinated Arenes with Isonitriles under UV-Light Irradiation. Chemistry (Weinheim an der Bergstrasse, Germany), 21(35), 12295-8. https://doi.org/10.1002/chem.201502298
Dewanji, Abhishek, et al. "C-F Activation in Perfluorinated Arenes with Isonitriles under UV-Light Irradiation." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,35 (2015): 12295-8. doi: https://doi.org/10.1002/chem.201502298
Dewanji A, Mück-Lichtenfeld C, Bergander K, Daniliuc CG, Studer A. C-F Activation in Perfluorinated Arenes with Isonitriles under UV-Light Irradiation. Chemistry. 2015 Aug 24;21(35):12295-8. doi: 10.1002/chem.201502298. Epub 2015 Jul 17. PMID: 26189958.
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Chemistry. 2015 Aug 24;21(35):12295-8. doi: 10.1002/chem.201502298. Epub 2015 Jul 17.

C-F Activation in Perfluorinated Arenes with Isonitriles under UV-Light Irradiation.

Chemistry (Weinheim an der Bergstrasse, Germany)

Abhishek Dewanji, Christian Mück-Lichtenfeld, Klaus Bergander, Constantin G Daniliuc, Armido Studer

Affiliations

  1. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany).
  2. Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany). [email protected].

PMID: 26189958 DOI: 10.1002/chem.201502298

Abstract

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 carbon-fluorine bond belongs to the strongest σ-bonds, which renders C-F activation highly challenging. Here it is shown that aryl and alkyl isonitriles efficiently activate the strong C-F bond in perfluoroarenes by simple UV irradiation under mild conditions. Reactions proceed by formal direct insertion of the isonitrile into the C-F bond without any transition metal. Activation occurs at arene C-F bonds whereas aliphatic C-F bonds remain unreacted. For selected perfluoroarenes C-F activation occurs with high regioselectivity and resulting imidoyl fluorides are transformed into other valuable compounds. Theoretical studies give insights into the reaction mechanism.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: CF activation; fluorine; perfluoroarene; photochemistry; transition-metal free

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