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

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Abstract

Several heterocycles reacted with shelf-stable 2-(2-fluoropyridinium-1-yl)-1,1-bis[(trifluoromethyl)sulfonyl] ethan-1-ide, a latent Tf2C[double bond, length as m-dash]CH2 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.

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

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Publication details

The article was received on 03 Sep 2018, accepted on 19 Sep 2018 and first published on 20 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00955D
Citation: Org. Chem. Front., 2018, Advance Article
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    Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles

    P. Almendros, H. Yanai, S. Hoshikawa, C. Aragoncillo, C. Lázaro-Milla, M. Toledano-Pinedo, T. Matsumoto and B. Alcaide, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00955D

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