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oai:docta.ucm.es:20.500.14352/919582025-03-18T11:53:48Zcom_20.500.14352_14col_20.500.14352_15

Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles Almendros Requena, Pedro Yanai, Hikaru Hoshikawa, Shoki Aragoncillo Abanades, Cristina Lázaro Milla, Carlos Toledano-Pinedo, Mireia Matsumoto, Takashi Alcaide Alañón, Benito 547 Heterocycles Triflyl group Ciencias Química orgánica (Química) 2306.10 Compuestos Heterocíclicos Several heterocycles reacted with shelf-stable 2-(2-fluoropyridinium-1-yl)-1,1-bis[(trifluoromethyl)sulfonyl] ethan-1-ide, a latent Tf2CvCH2 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. Ministerio de Economía, Comercio y Empresa (España) European Commission Depto. de Química Orgánica Fac. de Ciencias Químicas TRUE pub 2024-01-09T09:50:34Z 2024-01-09T09:50:34Z 2018 journal article VoR https://hdl.handle.net/20.500.14352/91958 2052-4129 10.1039/c8qo00955d eng (Projects CTQ2015-65060-C2-1-P and CTQ2015-65060- C2-2-P) Almendros P, Yanai H, Hoshikawa S, Aragoncillo C, Lázaro-Milla C, Toledano-Pinedo M, Matsumoto T, Alcaide B. Transition Metal-Free Controlled Synthesis of Bis[(Trifluoromethyl)Sulfonyl] Ethyl-Decorated Heterocycles. Org. Chem. Front. 2018, 5, 3163-3169. restricted access application/pdf Royal Society of Chemistry