1360544-12-2Relevant academic research and scientific papers
2-(Pyridinium-1-yl)-1,1-bis(perfluoroalkylsulfonyl)ethan-1-ide: A Practical Reagent for Synthesis of Strongly Acidic 1,1-Bis(perfluoroalkylsulfonyl)alkanes
Yanai, Hikaru,Takahashi, Ryuta,Takahashi, Yoichi,Kotani, Akira,Hakamata, Hideki,Matsumoto, Takashi
supporting information, p. 8203 - 8211 (2017/06/23)
On mixing (RfSO2)2CH2 (Rf=perfluoroalkyl), paraformaldehyde, and substituted pyridines, a three-component reaction proceeded smoothly to give unusual zwitterions bearing both pyridinium and stabilized carbanion moieties in good to excellent yields. Of these, 2-fluoropyridinium derivatives rapidly dissociated in acetonitrile to give equilibrium mixtures of the zwitterions and (RfSO2)2C=CH2/2-fluoropyridine, as confirmed by detailed variable-temperature NMR studies. The dynamic behavior of such 2-fluoropyridinium compounds allows them to be used as shelf-stable, easy-to-handle sources of (RfSO2)2C=CH2. With these reagents, strongly acidic carbon acids (RfSO2)2CHR were synthesized, which served as a new type of acid catalysts. Moreover, C?C bond-forming reactions with a ketene silyl acetal proceeded efficiently with Tf2C=CH2 generated in situ.
Bis(trifluoromethanesulfonyl)ethyl-bearing compound and acid catalyst, and method for preparing same
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Page/Page column 24, (2016/05/19)
A bis(trifluoromethanesulfonyl)ethyl group-bearing compound represented by the following formula [1], [2] or [3] .
An effective method to introduce carbon acid functionality: 2,2-bis(trifluoromethanesulfonyl)ethylation reaction of arenes
Yanai, Hikaru,Ogura, Hiroshi,Fukaya, Haruhiko,Kotani, Akira,Kusu, Fumiyo,Taguchi, Takeo
supporting information; experimental part, p. 11747 - 11751 (2011/11/06)
Introducing strong acids: The reaction of electron-rich arenes with Tf 2CHCH2CHTf2 (Tf=trifluoromethanesulfonyl; triflyl) smoothly gave 2,2-bis(triflyl)ethylated arenes. This reaction provides a convenient methodology for the introduction of a Tf2CH group, which is known to be a strongly Bronsted acidic functionality, to organic compounds in a regioselective manner (see scheme). On the basis of this reaction, significantly active and thermally stable carbon acid catalysts were developed.
