Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents

Gisnapp A, Trapp P, Schwabedissen J, Stammler H-G, Reichel M, Leitz D, Krumm B, Karaghiosoff K, Mitzel NW (2024)
Angewandte Chemie International Edition.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
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Autor*in
Gisnapp, Alexander; Trapp, PiaUniBi; Schwabedissen, JanUniBi; Stammler, Hans-GeorgUniBi; Reichel, Marco; Leitz, Dominik; Krumm, Burkhard; Karaghiosoff, Konstantin; Mitzel, Norbert W.UniBi
Abstract / Bemerkung
Fluoromethyl triflate (superfluoromethyl, SFM, FCH2OSO2CF3) and fluoromethyl fluorosulfonate (magic fluoromethyl, MFM, FCH2OSO2F) are two easily synthesized, highly effective and non-ozone depleting fluoromethylation reagents. They are analogous to the well-known and widely used methylation re-agents CH3OSO2CF3 and CH3OSO2F. Both SFM and MFM have been fully characterized by multinuclear NMR spectroscopy (1H, 13C, 17O, 19F, 33S). Their structures have been determined in the solid state on in situ grown crystals by X-ray diff-raction and in the gas phase by electron diffraction. The fluoromethylation efficiency of SFM and MFM was shown by reaction with chalcogen nucleophiles of differing nucleophilicity. All fluoromethylated products were isolated as pure com-pounds and charac-terized by NMR and vibrational spec-troscopy, as well as in some cases by single crystal X-ray diffraction. © 2024 Wiley‐VCH GmbH.
Erscheinungsjahr
2024
Zeitschriftentitel
Angewandte Chemie International Edition
eISSN
1521-3773
Page URI
https://pub.uni-bielefeld.de/record/2999936

Zitieren

Gisnapp A, Trapp P, Schwabedissen J, et al. Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents. Angewandte Chemie International Edition. 2024.
Gisnapp, A., Trapp, P., Schwabedissen, J., Stammler, H. - G., Reichel, M., Leitz, D., Krumm, B., et al. (2024). Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.202420540
Gisnapp, Alexander, Trapp, Pia, Schwabedissen, Jan, Stammler, Hans-Georg, Reichel, Marco, Leitz, Dominik, Krumm, Burkhard, Karaghiosoff, Konstantin, and Mitzel, Norbert W. 2024. “Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents”. Angewandte Chemie International Edition.
Gisnapp, A., Trapp, P., Schwabedissen, J., Stammler, H. - G., Reichel, M., Leitz, D., Krumm, B., Karaghiosoff, K., and Mitzel, N. W. (2024). Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents. Angewandte Chemie International Edition.
Gisnapp, A., et al., 2024. Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents. Angewandte Chemie International Edition.
A. Gisnapp, et al., “Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents”, Angewandte Chemie International Edition, 2024.
Gisnapp, A., Trapp, P., Schwabedissen, J., Stammler, H.-G., Reichel, M., Leitz, D., Krumm, B., Karaghiosoff, K., Mitzel, N.W.: Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents. Angewandte Chemie International Edition. (2024).
Gisnapp, Alexander, Trapp, Pia, Schwabedissen, Jan, Stammler, Hans-Georg, Reichel, Marco, Leitz, Dominik, Krumm, Burkhard, Karaghiosoff, Konstantin, and Mitzel, Norbert W. “Fluoromethyl Triflate and Fluoromethyl Fluorosulfonate: Easily Accessible and Powerful Fluoromethylation Reagents”. Angewandte Chemie International Edition (2024).

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