13630-19-8Relevant articles and documents
One-pot sandmeyer trifluoromethylation and trifluoromethylthiolation
Bayarmagnai, Bilguun,Matheis, Christian,Risto, Eugen,Goossen, Lukas J.
, p. 2343 - 2348 (2014)
Practical one-pot procedures were developed for both Sandmeyer-type trifluoromethylations and trifluoromethylthiolations. Starting from broadly available (hetero)aromatic amines, various benzotrifluorides were synthesized in high yields via in situ diazotization and copper-mediated trifluoromethylation using the inexpensive Ruppert-Prakash trifluoromethylating reagent. In the presence of sodium thiocyanate as a sulfur source, aryl trifluoromethyl thioethers are exclusively formed.
Synthesis of 2-methyl-1,5-dinitro-3- and 2-methyl-1,3-dinitro-5-(trifluoromethyl)benzenes and their transformation into 6-nitro-4-(trifluoromethyl)- and 4-nitro-6-(trifluoromethyl)-1H-indoles
Petruk, Oksana M.,Kyriukha, Yevhenii A.,Bezdudny, Andriy V.,Rozhkov, Vladimir V.
, p. 176 - 179 (2015)
A facile two-step synthesis of 2-methyl-1,5-dinitro-3- and 2-methyl-1,3-dinitro-5-(trifluoromethyl)benzenes is described. The first step is the nitration of otho- and para-methylbenzoic acids to furnish the corresponding dinitroacids. The dinitroacids then react with sulfur tetrafluoride to provide the corresponding trifluoromethylated products. The latter are easily transformed into 6-nitro-4-(trifluoromethyl)- and 4-nitro-6-(trifluoromethyl)-1H-indoles by applying the Batcho-Leimgruber synthetic protocol.
Flash Thermolysis of Aryl Trifluoroacetates: A New Approach to Trifluoromethylated Aromatic Compounds
Kobayashi, Y.,Nakazato, A.,Kumadaki, I.,Filler, R.
, p. 467 - 470 (1986)
Flash thermolysis of aryl trifluoroacetates yield trifluoromethyl aromatic compounds along with trifluoromethoxy compounds.
Use of methyllithium in metal/halogen exchange; a mild and efficient method for the synthesis of ortho substituted toluenes
Andrews,Kitteringham,Voyle
, p. 2323 - 2327 (2001)
Methyllithium, in the presence of excess methyl iodide, can be used to convert suitably substituted aromatic bromides to the corresponding toluenes under mild conditions and in high yield.
Ligand-free trifluoromethylation of iodoarenes by use of 2-Aryl-2-trifluoromethylbenzimidazoline as new trifluoromethylating reagent
Miyagawa, Masamichi,Ishikawa, Taisuke,Shinkai, Kota,Akiyama, Takahiko
, p. 29 - 31 (2019)
N-Methyl 2-aryl-2-trifluoromethylbenzimidazolines were synthesized and utilized in the trifluoromethylation reaction of iodoarenes in the presence of copper(I) salt and base. Iodoarenes bearing electron-donating and electron-withdrawing groups were tolerant to this reaction in the absence of a ligand and gave trifluorotoluene derivatives in good to high yields.
Pregeneration, Spectroscopic Detection, and Chemical Reactivity of (Trifluoromethyl)copper, an Elusive and Complex Species
Wiemers, Denise M.,Burton, Donald J.
, p. 832 - 834 (1986)
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Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source
Kariofillis, Stavros K.,Shields, Benjamin J.,Tekle-Smith, Makeda A.,Zacuto, Michael J.,Doyle, Abigail G.
supporting information, p. 7683 - 7689 (2020/04/22)
Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
The first nucleophilic C-H perfluoroalkylation of aromatic compounds via (arene)tricarbonylchromium complexes
Kirij, Natalia V.,Filatov, Andrey A.,Khrapach, Gleb Yu.,Yagupolskii, Yurii L.
supporting information, p. 2146 - 2149 (2017/02/19)
The first nucleophilic perfluoroalkylation of arenes is based on the arene π-system activation via (η6-arene)tricarbonylchromium complexes. Perfluoroalkyl anions generated from Me3SiRF and a fluoride ion source [Me4N]F exclusively attack the arene ligand under mild conditions. The formed negatively charged analogs of Meisenheimer adducts readily undergo a one-pot oxidation to perfluoroalkyl arenes.
