%0 Journal Article
%A Almendros Requena, Pedro
%A Yanai, Hikaru
%A Hoshikawa, Shoki
%A Aragoncillo Abanades, Cristina
%A Lázaro Milla, Carlos
%A Toledano-Pinedo, Mireia
%A Matsumoto, Takashi
%A Alcaide Alañón, Benito
%T Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles
%D 2018
%@ 2052-4129
%U https://hdl.handle.net/20.500.14352/91958
%X 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.
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