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Título: | Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles |
Autor: | Almendros, Pedro CSIC ORCID ; Yanai, H.; Hoshikawa, S.; Aragoncillo, Cristina CSIC ORCID; Lázaro-Milla, C.; Toledano-Pinedo, M. CSIC ORCID; Matsumoto, T.; Alcaide, Benito CSIC ORCID | Fecha de publicación: | 2018 | Editor: | Royal Society of Chemistry (UK) | Citación: | Organic Chemistry Frontiers 5: 3163-3169 (2018) | Resumen: | Several heterocycles reacted with shelf-stable 2-(2-fluoropyridinium-1-yl)-1,1-bis[(trifluoromethyl)sulfonyl] ethan-1-ide, a latent TfCCH source, to give rise in a mild and controllable way to adducts via direct C-H bis[(trifluoromethyl)sulfonyl]ethylation reactions. This metal- and irradiation-free protocol is convenient. Besides, the volatile side-product 2-fluoropyridine can be smoothly eliminated under vacuum, which facilitates purification. The substrate scope survey discloses that exquisite chemo- and regioselectivities are achieved in a variety of heterocyclic systems. Of particular interest are the late-stage structural modification of known pharmaceuticals, such as the marketed drugs Phenazone (Antipyrine) and Edaravone, and the development of a water soluble fluorescent dye. | URI: | http://hdl.handle.net/10261/173959 | DOI: | 10.1039/c8qo00955d | Identificadores: | doi: 10.1039/c8qo00955d issn: 2052-4110 e-issn: 2052-4129 |
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