RT Journal Article
T1 Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles
A1 Almendros Requena, Pedro
A1 Yanai, Hikaru
A1 Hoshikawa, Shoki
A1 Aragoncillo Abanades, Cristina
A1 Lázaro Milla, Carlos
A1 Toledano-Pinedo, Mireia
A1 Matsumoto, Takashi
A1 Alcaide Alañón, Benito
AB 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.
PB Royal Society of Chemistry
SN 2052-4129
YR 2018
FD 2018
LK https://hdl.handle.net/20.500.14352/91958
UL https://hdl.handle.net/20.500.14352/91958
LA eng
NO 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.
NO Ministerio de Economía, Comercio y Empresa (España)
NO European Commission
DS Docta Complutense
RD 31 ago 2024