55204-33-6Relevant academic research and scientific papers
Iron porphyrin-catalyzedN-trifluoroethylation of anilines with 2,2,2-trifluoroethylamine hydrochloride in aqueous solution
Guo, Cancheng,Guo, Yongjia,Liu, Qiang,Ren, Shuang,Xu, Guiming
, p. 20322 - 20325 (2021/06/26)
An iron porphyrin-catalyzedN-trifluoroethylation of anilines has been developed with 2,2,2-trifluoroethylamine hydrochloride as the fluorine source. This one-pot N-H insertion reaction is conductedviacascade diazotization/N-trifluoroethylation reactions.
Direct N-Alkylation/Fluoroalkylation of Amines Using Carboxylic Acids via Transition-Metal-Free Catalysis
Lu, Chunlei,Qiu, Zetian,Xuan, Maojie,Huang, Yan,Lou, Yongjia,Zhu, Yiling,Shen, Hao,Lin, Bo-Lin
supporting information, p. 4151 - 4158 (2020/08/21)
A scalable protocol of direct N-mono/di-alkyl/fluoroalkylation of primary/secondary amines has been constructed with various carboxylic acids as coupling agents under the catalysis of a simple air-tolerant inorganic salt, K3PO4. Advantageous features include 100 examples, 10 drugs and drug-like amines, fluorinated complex tertiary amines, gram-scale synthesis and isotope-labelling amine, thus demonstrating the potential applicability in industry of this methodology. The involvement of relatively less reactive silicon-hydride compared with the traditional reactive metal-hydride or boron-hydride species required to reduce the amide intermediates presumably contributes to the remarkable functional group compatibility. (Figure presented.).
Method of catalyzing trifluoro-ethylation of aromatic secondary amine by ferriporphyrin
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Paragraph 0046-0084, (2019/01/08)
The invention provides a method of catalyzing trifluoro-ethylation of aromatic secondary amine by ferriporphyrin. The method comprises the following steps: adding trifluoroethylamine salt and nitriteto a diazo-reaction first and then adding aromatic prima
Transition metal-free: N -fluoroalkylation of amines using cyanurate activated fluoroalcohols
Haghighi, Fatemeh,Panahi, Farhad,Golbon Haghighi, Mohsen,Khalafi-Nezhad, Ali
supporting information, p. 12650 - 12653 (2017/12/02)
A novel and highly efficient method for N-fluoroalkylation of amines using 2,4,6-tris(fluoroalkoxy)-1,3,5-triazines was developed. This simple approach allowed the N-fluoroalkylation of amines under fast, mild and efficient reaction conditions, without using a transition metal as a catalyst.
Trifluoroacetaldehyde: A useful industrial bulk material for the synthesis of trifluoromethylated amino compounds
Mimura, Hideyuki,Kawada, Kosuke,Yamashita, Tetsuya,Sakamoto, Takeshi,Kikugawa, Yasuo
experimental part, p. 477 - 486 (2010/05/02)
The synthesis of various trifluoromethylated amino compounds was studied using trifluoroacetaldehyde, an industrial bulk material, as a starting compound. One general application of trifluoroacetaldehyde is the preparation of trifluoroethylamino derivatives via reductive amination reaction. This synthesis includes the formation of the corresponding N,O-acetal intermediates followed by their reduction using NaBH4 or 2-picoline borane complex, affording the target trifluoroethylamino compounds in moderate to good yields (47-87%). Another general application of trifluoroacetaldehyde is the synthesis of chiral α-substituted trifluoroethylamino compounds. In this synthesis, trifluoroacetaldehyde was first converted into the chiral trifluoromethyl tert-butyl sulfinimine, which was subjected to 1,2-nucleophilic addition reactions across its C{double bond, long}N double bond. The addition of phenyllithium afforded α-(phenyl)trifluoroethylamino derivative in 83% yield and with 96% de. Allylation and Reformatsky reactions produced the corresponding α-substituted trifluoroethylamino derivatives in 82 and 58% yields and with 90 and 91% de, respectively.
Electrolytic Reactions of Fluoroorganic Compounds. 14. Regioselective Anodic Methoxylation of N-(Fluoroethyl)amines. Preparation of Highly Useful Fluoroalkylated Building Blocks
Fuchigami, Toshio,Ichikawa,, Shinji
, p. 607 - 615 (2007/10/02)
Anodic methoxylation of various types of N-(fluoroethyl)amines, ArRNCH2Rf (Rf = CF3, CHF2, CH2F, etc.) has been systematically studied and it was found that a methoxy group was exclusively or preferentially introduced into the position α to the fluoromethyl (Rf) group, depending on the Rf and R groups.The effect of the Rf group on the promotion of the anodic α-methoxylation decreased in the order CF3, CHF2, and CH2F.This remarkable promotion effect and unique regioselectivity can be explained mainly in terms of the α-CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines.The α-methoxylated products are highly useful precursors for the construction of carbon-carbon bonds α to the trifluoromethyl and difluoromethyl groups, which is difficult by other methods.
Electrolytic Transformation of Fluoroorganic Compounds. 3. Highly Regioselective Anodic Methoxylation of N-(2,2,2-trifluoroethyl)amines
Fuchigami, Toshio,Nakagawa, Yuuki,Nonaka, Tsutomu
, p. 5489 - 5491 (2007/10/02)
Anodic methoxylation of N-alkyl-N-(2,2,2-trifluoroethyl)anilines and N-(2,2,2-trifluoroethyl)diphenylamine places the methoxy group in the α-position (toward the trifluoromethyl group); these products are useful building blocks for the construction of a c
ON THE REACTION OF INDOLE WITH SODIUM BOROHYDRIDE IN TRIFLUOROACETIC ACID
Gribble, Gordon W.,Nutaitis, Charles F.,Leese, Robert M.
, p. 379 - 386 (2007/10/02)
The reaction of indole (1) with sodium borohydride in trifluoroacetic acid gives, successively, indoline (3), N-(2,2,2-trifluoroethyl)indoline (4), and 1,1,1-trifluoro-2,2-bisethane (5), whose structure is established by chemical and spectral means.Similar reactions are observed with N-methylaniline (8) and anisole, but not with dibenzazepines 13 and 15, which give only N-trifluoroethylation.
