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
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.
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.
