718-35-4Relevant academic research and scientific papers
Deoxofluorination of (Hetero)aromatic Acids
Alekseenko, Anatoliy N.,Bugera, Maksym Ya.,Gerus, Igor I.,Kiriakov, Oleksandr,Klipkov, Anton A.,Mykhailiuk, Pavel K.,Pustovit, Yurii,Razhyk, Bohdan,Semenov, Sergey,Starova, Viktoriia S.,Tananaiko, Oksana Yu.,Tarasenko, Karen,Tolmachev, Andrei A.,Trofymchuk, Serhii,Zaporozhets, Olga A.
, p. 3110 - 3124 (2020/03/23)
Diverse trifluoromethyl-substituted compounds were synthesized by deoxofluorination of cinnamic and (hetero)aromatic carboxylic acids with sulfur tetrafluoride. The obtained products were used as starting materials in the preparation of novel fluorinated amino acids, anilines, and aliphatic amines - valuable building blocks for medicinal chemistry and agrochemistry.
Cu(III)-CF3 Complex Enabled Unusual (Z)-Selective Hydro-trifluoromethylation of Terminal Alkynes
Zhang, Song-Lin,Xiao, Chang
, p. 10908 - 10915 (2018/09/06)
An efficient and selective hydro-trifluoromethylation of terminal alkynes is developed to enable the synthesis of 1,2-disubstituted trifluoromethylated Z-alkenes from terminal alkynes, a silane and a Cu(III)-CF3 complex in DMF. The unusual Z-selectivity and the compatibility of various functional groups make this reaction complementary to previous vinyl-CF3 bond-forming methods producing dominantly E-products or a mixture of E,Z-isomers. Extensive mechanistic studies indicate that this reaction may involve a key step of migratory insertion of initially formed Ar-C-C-CF3 into LCu(I)-H intermediate and subsequent hydrogenation of the vinyl-copper species to give finally the Z-trifluoromethylated styrenes. Deuterium labeling experiments show that DMF acts not merely as the solvent but also as the source of α-H in the Z-trifluoromethylated styrene products. Given the novel syn-difunctionalization of alkynes using Cu(III)-CF3 complexes/a nucleophilic reagent we developed recently that are also in contrast to the previous anti-difunctionalization chemistry, Cu(III)-CF3 complexes are demonstrated to show distinct reactivity properties compared to conventional CF3 reagents (Togni's reagents and Umemoto-type reagents) and may thus enable the development of other interesting reactions.
Microwave-assisted preparation of trifluoroacetaldehyde (fluoral): isolation and applications
Landge, Shainaz M.,Borkin, Dmitry A.,T?r?k, Béla
, p. 6372 - 6376 (2008/02/12)
A novel method for the preparation of trifluoroacetaldehyde (fluoral, TFAc, CF3CHO) from commercially available trifluoroacetaldehyde ethylhemiacetal (TFAE) by microwave irradiation is described. The isolation, characterization and reaction of fluoral with various nucleophiles were studied to verify the diverse applicability of this new method.
Hydrolysis of hydroxybenzotrifluorides and fluorinated uracil derivatives. A general mechanism for carbon fluorine bond labilization
Sakai,Santi
, p. 1079 - 1084 (2007/10/09)
The kinetics of hydrolysis of o and p hydroxybenzotrifluoride (1 and 2) and 1 trifluoromethyl 2 (4 hydroxyphenyl) ethylene (3) and the uracil derivatives 5 difluoromethyluracil (5) and 1 methyl 5 difluoromethyluracil (6) are described. Compounds 1 and 2 h
