Transition metal catalyzed trifluoromethylation reactions
DOI:
https://doi.org/10.54167/tecnociencia.v16i1.838Keywords:
Trifluoromethylation, Transition metals , catalyst., trifluoromethylation, transition metals, catalystAbstract
The trifluoromethylation reactions have great importance in the pharmaceutical industry due to the properties they confer to the compounds having this functional group. These kind of reactions are present in the elaboration of synthons as the key structural units to produce Aprepitant, Fluoxetine, Leflunomide and Dutasteride, having great impact on the pharmaceutical industry. The text summarizes the different reagents used in trifluoromethylation, highlighting the relevance of transition metal catalyzed reactions in obtaining cheaper and cleaner processes.
Downloads
References
Bazyar, Z. & Hosseini-Sarvari, M. (2019). Au@ZnO Core-shell: Scalable photocatalytic trifluoromethylation using CF3COONa as an inexpensive reagent under visible light irradiation. Organic Process Research & Development, 23, 2345-2353. https://doi.org/10.1021/acs.oprd.9b00225
Chang, Y. & Cai, C. (2005). Trifluoromethylation of carbonyl compounds with sodium trifluoroacetate. Journal of Fluorine Chemistry, 126, 937-940. https://doi.org/10.1016/j.jfluchem.2005.04.012
Cotté, A., Gotta, M., Beller, M., Schareina, T., Zapf, A., Wu, X-F. (2013). Copper-catalysed process for the production of substituted or unsubstituted trifluormethylated aryl and heteroaryl compounds. US Patent. No. 8,530,666 B2. https://patents.google.com/patent/US8530666B2/en
Dubinina, G., Furutachi, H., & Vicic, D.A. (2008). Active trifluoromethylating agents from well-defined Copper(I)-CF3 complexes. Journal of the American Chemical Society, 130, 8600-8601. https://doi.org/10.1021/ja802946s
Hu, W.-Q., Pan, S., Xu, X.-H., Vicic, D.A., & Qing, F.-L. (2020). Nickel-mediated trifluoromethylation of phenol derivatives by aryl C-O bond activation. Angewandte Chemie, 59,37, 16076-16082. https://doi.org/10.1002/anie.202004116
Johansen, M.B. & Linhardt, A.T. (2020). Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides. Organic & Biomolecular Chemistry 18, 1415-1225. https://doi.org/10.1039/C9OB02635E
Kiyohide, M., Etsuko, T., Midori, A., Kiyosi, K. (1981). A convenient trifluoromethylation of aromatic halides with sodium trifluoroacetate. Chemistry Letters, 10, 1719-1720. https://doi.org/10.1246/cl.1981.1719
McLoughlin, V.C.R. & Thrower, J. (1968). Manufacture of organic compounds containing fluorine. US Patent No. 3,408,411A. https://patents.google.com/patent/US3408411A/en
Lecturas complementarias
Alonso, C., Martínez de Marigorta, E., Rubiales, G. & Palacios, F. (2015). Carbon trifluoromethylation reactions of hydrocarbon derivatives and heteroarenes. Chemical Reviews, 115, 1847−1935. https://doi.org/10.1021/cr500368h
Ashton, T.D., Devine, S.M., Mòhrle, J.J., Laleu, B., Burrows, J.N., Charman, S.A., Creek, D.J. & Sleebs, B.E. (2019). The development process for discovery and clinical advancement of modern antimalarials. Journal of Medicinal Chemistry, 62, 10526–10562. https://doi.org/10.1021/acs.jmedchem.9b00761
Ball, N.D., Kampf, J.W. & Sanford, M.S. (2010). Aryl-CF3 Bond-forming reductive elimination from palladium (IV). Journal of the American Chemical Society, 132, 2878-2879. https://doi.org/10.1021/ja100955x
McReynolds, K.A., Lewis, R.S., Ackerman, L.K.G., Dubinina, G.G., Brennessel, W.W. & Vicic, D.A. (2010). Decarboxylative trifluoromethylation of aryl halides using well-defined copper–trifluoroacetate and –chlorodifluoroacetate precursors. Journal of Fluorine Chemistry, 131, 1108–1112. https://doi.org/10.1016/j.jfluchem.2010.04.005
Nakamura, Y., Fujio, M., Murase, T., Itoh, Y., Serizawa, H., Aikawa, K. & Mikami, K. (2013). Cu-catalyzed trifluoromethylation of aryl iodides with trifluoromethylzinc reagent prepared in situ from trifluoromethyl iodide. Beilstein Journal of Organic Chemistry 9, 2404-2409. https://doi.org/10.3762/bjoc.9.277
Schiesser, S., Chepliaca, H., Kollback, J., Quennesson, T., Czechtizky, W. & Cox, R.J. (2020). N-trifluoromethyl amines and azoles: An underexplored functional group in the Medicinal Chemist’s Toolbox. Journal of Medicinal Chemistry, 63, 13076–13089. https://doi.org/10.1021/acs.jmedchem.0c01457
Tomashenko, O.A. & Grushin, V.V. (2011). Aromatic trifluoromethylation with metal complexes. Chemical Reviews, 111, 4475–4521. https://doi.org/10.1021/cr1004293
Wang, J., Sánchez-Rosello, M., Aceña, J.L., del Pozo, C., Sorochinsky, A.E., Fustero, S., Soloshonok, V.A., & Liu, H. (2014). Fluorine in pharmaceutical industry: Fluorine-containing drugs introduced to the market in the last decade (2001-2011). Chemical Reviews 114, 2432-2506. https://doi.org/10.1021/cr4002879
Wenthur, C.J., Bennett, M.R., & Lindsley, C.W. (2014). Classics in chemical neuroscience: Fluoxetine (Prozac). ACS Chemical Neuroscience 5(1), 14-23. https://doi.org/10.1021/cn400186j
Zhang, C. (2014). Recent advances in trifluoromethylation of organic compounds using Umemoto`s reagents. Organic & Biomolecular Chemistry 12, 6580-6589. https://doi.org/10.1039/C4OB00671B
Downloads
Published
Issue
Section
License
Copyright (c) 2022 TECNOCIENCIA Chihuahua
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.
