- Trifluoromethanesulfonic Anhydride as a Low-Cost and Versatile Trifluoromethylation Reagent
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A large number of reagents have been developed for the synthesis of trifluoromethylated compounds. However, an ongoing challenge in trifluoromethylation reaction is the use of less expensive and practical trifluoromethyl sources. We report herein the unprecedented direct trifluoromethylation of (hetero)arenes using trifluoromethanesulfonic anhydride as a radical trifluoromethylation reagent by merging photoredox catalysis and pyridine activation. Furthermore, introduction of both the CF3 and OTf groups of the trifluoromethanesulfonic anhydride into internal alkynes to access tetrasubstituted trifluoromethylated alkenes was achieved. Since trifluoromethanesulfonic anhydride is a low-cost and abundant chemical, this method provides a cost-efficient and practical route to trifluoromethylated compounds.
- Ouyang, Yao,Xu, Xiu-Hua,Qing, Feng-Ling
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supporting information
p. 6926 - 6929
(2018/05/07)
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- Inhibition of HIV-1 capsid assembly: Optimization of the antiviral potency by site selective modifications at N1, C2 and C16 of a 5-(5-furan-2-yl-pyrazol- 1-yl)-1H-benzimidazole scaffold
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A uHTS campaign led to the discovery of a 5-(5-furan-2-ylpyrazol-1-yl)-1H- benzimidazole series that inhibits assembly of HIV-1 capsid. Synthetic manipulations at N1, C2 and C16 positions improved the antiviral potency by a. The X-ray structure of 33 complexed with the capsid N-terminal domain allowed identification of major interactions between the inhibitor and the protein.
- Tremblay, Martin,Bonneau, Pierre,Bousquet, Yves,Deroy, Patrick,Duan, Jianmin,Duplessis, Martin,Gagnon, Alexandre,Garneau, Michel,Goudreau, Nathalie,Guse, Ingrid,Hucke, Oliver,Kawai, Stephen H.,Lemke, Christopher T.,Mason, Stephen W.,Simoneau, Bruno,Surprenant, Simon,Titolo, Steve,Yoakim, Christiane
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p. 7512 - 7517
(2013/02/23)
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- SYNTHESIS AND POLYMERISATION OF ETHYNYLTHIOPHENES AND ETHYNYLFURANS CONTAINING TRIFLUORMETHYL GROUPS
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Fluorination of thiophenedicarboxylic acid with sulfur tetrafluoride in the presence of anhydrous hydrogen fluoride provided mono and bis(trifluoromethyl)thiophenes in moderate yields.Ethynylthiophenes and ethynylfurans containing trifluoromethyl groups were prepared via 2,2-dichloro-1-fluorovinyl compounds.In polymerizations using transitions metal catalysts, 3-ethynylthiophenes gave polymers in high yields, which were soluble in THF and/or fluorocompounds, while 2-ethynylthiophenes polymerized in low yields.In γ-ray induced polymerization, only 2,5-bis(trifluoromethyl)-3-ethynylthiophene afforded the corresponding polymers.Thermal decomposition temperatures of polymers obtained increased by introduction of the trifluoromethyl groups as well as the methyl groups.
- Nishida, Masakazu,Fujii, Shozo,Aoki, Toshiki,Hayakawa, Yoshio,Muramatsu, Hiroshige,Morita, Tomohiko
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p. 445 - 459
(2007/10/02)
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