65715-20-0Relevant articles and documents
Bromodifluoromethylation of heteroaromatics with sodium bromodifluoromethanesulfinate
Zhang, Jin,Xu, Xiu-Hua,Qing, Feng-Ling
, p. 2462 - 2464 (2016)
The bromodifluoromethylation of heteroaromatics (benzofuran, benzo[b]thiophene, and 2H-chromen-2-one) with sodium bromodifluoromethanesulfinate (BrCF2SO2Na) was developed. This reaction proceeded smoothly at room temperature to affor
Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex
Cantillo, David,Jud, Wolfgang,Kappe, C. Oliver,Maljuric, Snjezana
supporting information, (2019/10/08)
While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.
Au@ZnO Core-Shell: Scalable Photocatalytic Trifluoromethylation Using CF3CO2Na as an Inexpensive Reagent under Visible Light Irradiation
Bazyar, Zahra,Hosseini-Sarvari, Mona
supporting information, p. 2345 - 2353 (2019/10/16)
Trifluoromethylation is of significant importance for the synthesis of many small molecules vital for medicinal and agrochemical research. The importance of the CF3 group as well as the related synthetic challenges is so evident that many reagents have been reported for the synthesis of trifluoromethylated compounds, but these typical reagents are expensive and the methods for preparing them are difficult. Here, we report a new scalable and operationally simple trifluoromethylation reaction using sodium trifluoroacetate as a reagent and Au-modified ZnO as a photocatalyst under visible light irradiation. The reaction proceeds via trifluoromethylation of a broad range of aryl halides, arylboronic acids, and arene and heteroarene substrates. Some pharmaceutical and agrochemical compounds have been trifluoromethylated directly to demonstrate the applicability of the method.
Catalytic trifluoromethylation of aryl- and vinylboronic acids by 2-cyclopropyl-1-(trifluoromethyl)benzo[ b ]thiophenium triflate
Arimori, Sadayuki,Shibata, Norio
supporting information, p. 1632 - 1635 (2015/04/14)
Catalytic trifluoromethylation of aryl- and vinylboronic acids by 2-cyclopropyl-1-(trifluoromethyl)benzo[b]thiophenium triflate is described. In the presence of a catalytic amount of CuOAc and 2,4,6-collidine in ethyl acetate, the reaction proceeded in good to high yields for various substrates under mild reaction conditions at room temperature.
Effects of B2pin2 and PCy3 on copper-catalyzed trifluoromethylation of substituted alkenes and alkynes with the Togni reagent
Janson, P?r G.,Ilchenko, Nadia O.,Diez-Varga, Alberto,Szabó, Kálmán J.
, p. 922 - 931 (2015/03/30)
The copper-catalyzed oxytrifluoromethylation of phenylacetylenes and C-H trifluoromethylation of quinones were studied. It was found that both reactions are accelerated by B2pin2 and PCy3 additives. The two reactions have different substituent effects. The oxytrifluoromethylation is faster in the presence of electron-donating groups, while the C-H trifluoromethylation is faster with electron-withdrawing substituents. The Hammett plot for oxytrifluoromethylation gave a ρ value of -0.76 indicating electron demand in the rate determining step of the reaction. According to the absolute value of ρ the reaction probably does not proceed through a rate determining formation of a carbocation intermediate. The kinetic isotope effect measurements indicate that in C-H trifluoromethylation of quinones the cleavage of the C-H bond is not the rate determining step of the reaction.
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted decomposition of difluorocarbene and the subsequent trifluoromethylation
Zheng, Jian,Lin, Jin-Hong,Deng, Xiao-Yun,Xiao, Ji-Chang
, p. 532 - 535 (2015/03/04)
Difluorocarbene derived from various carbene precursors could be effectively decomposed by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). This decomposition process was successfully applied in the subsequent trifluoromethylation of a variety of (hetero)aryl iodides without the addition of an external fluoride ion. Mechanistic investigation revealed the detailed difluorocarbene conversion process in which the decomposed difluorocarbene is finally transformed into a fluoride ion and carbon monoxide.
Metal-free radical perfluoroalkylation of (hetero)arenes
Zhong, Sabilla,Hafner, Andreas,Hussal, Christoph,Nieger, Martin,Br?se, Stefan
, p. 6255 - 6258 (2015/02/19)
We report a metal-free radical perfluoroalkylation method which uses inexpensive and commercially available perfluorocarboxylic anhydrides as an easy to use source of perfluoroalkyl radicals. This approach allows the perfluoroalkylation of different arenes, such as benzene derivatives, furans, thiophenes, and pyrroles, including highly functionalized compounds.
Copper-mediated trifluoromethylation of aryl-, heteroaryl-, and vinyltrifluoroborates with Langlois' reagent
Dubbaka, Srinivas Reddy,Salla, Manohar,Bolisetti, Raghu,Nizalapur, Shashidhar
, p. 6496 - 6499 (2014/02/14)
An effortless and realistic procedure for the copper-mediated trifluoromethylation of aryl-, heteroaryl- and vinyltrifluoroborates with CF3 radicals generated from NaSO2CF3 and tert-butyl hydroperoxide (TBHP) is presented. The developed method produces trifluoromethyl arenes and -alkenes in good to excellent yields and a wide range of electronically and structurally diverse substrates are tolerated.
Copper-mediated radical trifluoromethylation of unsaturated potassium organotrifluoroborates
Presset, Marc,Oehlrich, Daniel,Rombouts, Frederik,Molander, Gary A.
, p. 12837 - 12843 (2014/01/17)
Copper-mediated trifluoromethylation of unsaturated organotrifluoroborates with the Langlois reagent (NaSO2CF3) and TBHP allows the introduction of trifluoromethyl groups into a variety of organic substructures. The reactions are easy to set up, the conditions are mild and general, and the process provides access to trifluoromethylated alkynes, alkenes, arenes, and heteroarenes in fair to good yields.
Copper-catalyzed trifluoromethylation of aryl- and vinylboronic acids with generation of CF3-radicals
Li, Yang,Wu, Lipeng,Neumann, Helfried,Beller, Matthias
supporting information, p. 2628 - 2630 (2013/04/23)
The selective trifluoromethylation of aryl- and vinylboronic acids proceeds smoothly with CF3SO2Na (Langlois reagent) in the presence of copper catalysts and t-BuOOH. Therefore, the method relies both on transition metal catalysis an
