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

Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles

Official URL

https://doi.org/10.1039/c8qo00955d

Publication date

2018

Authors

Almendros Requena, Pedro

Yanai, Hikaru

Hoshikawa, Shoki

Aragoncillo Abanades, Cristina

Lázaro Milla, Carlos

Toledano-Pinedo, Mireia

Matsumoto, Takashi

Alcaide Alañón, Benito

Publisher

Royal Society of Chemistry

Citations

Exportar

URI

https://hdl.handle.net/20.500.14352/91958

Citation

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.

Abstract

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.