cas 75999-66-5, 2,2,2-TRIFLUORO-N-(4-METHOXY-PHENYL)-ACETIMIDOYL CHLORIDE

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Silver-Mediated [3 + 2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles
A silver-mediated [3 + 2] cycloaddition of azomethine ylides with trifluoroacetimidoyl chlorides for the rapid assembly of 5-(trifluoromethyl)imidazoles has been developed. Notable features of the reaction include readily accessible reagents, a broad substrate scope, and high efficiency. The protocol can be successfully applied to construct the analogue of the specific allosteric modulator of GABAA receptors. The silver species could be recycled by a simple operation.
Yang, Hefei,Lu, Shu-Ning,Chen, Zhengkai,Wu, Xiao-Feng
supporting information
p. 4361 - 4370
(2021/03/09)

Palladium-catalyzed synthesis of novel trifluoromethylated quinazolinone, N-arylquinazoline and N-benzylquinazoline derivatives
A simple and palladium-catalyzed procedure for synthesis of a novel series of potentially biologically active trifluoromethyl-substituted quinazolinones and N-arylquinazoline derivatives via condensation-cyclization reaction of 2-aminobenzamide, 2-amino-N′-arylbenzimidamides and 2-amino-N′-benzylbenzimidamides with trifluoroacetimidoyl chlorides has been developed. noteworthy, this investigation showed the possible of transition-metal-catalyzed activation of trifluoroacetimidoyl chlorides as a carbon trifluoromethylated source for the synthesis of quinazolines and quinazolinone derivatives in good to excellent yields.
Sajadi, Mahdieh Sadat,Kazemi, Elham,Darehkordi, Ali
supporting information

(2021/04/23)

Synthesis of 5-Trifluoromethyl-1,2,4-Triazoles via Metal-Free Annulation of Trifluoroacetimidohydrazides and Methyl Ketones
A metal-free approach for the synthesis of 5-trifluoromethyl-1,2,4-triazoles via I2-mediated [4+1] annulation of readily available trifluoroacetimidohydrazides and methyl ketones has been achieved. The transformation involves iodination/Kornblum oxidation, intermolecular dehydration condensation and an iodine-mediated intramolecular cyclization/aromatization sequence. The developed protocol can be easily scaled up to 3 mmol scale without obvious efficiency decrease and be implemented by a consecutive one-pot manner. (Figure presented.).
Chen, Zhengkai,Tang, Jianhua,Wu, Xiao-Feng,Zhang, Jiajun
p. 3060 - 3069
(2021/05/10)

The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines
A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines andN-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.
Chen, Zhengkai,Du, Shiying,Song, Yufei,Wang, Le-Cheng,Wu, Xiao-Feng
supporting information
p. 6115 - 6119
(2021/07/21)

Annulation of CF3-Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles
A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, and the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have been obtai
Wen, Si,Tian, Qingyu,Chen, Yanhui,Zhang, Yuqing,Cheng, Guolin
supporting information
p. 7407 - 7411
(2021/10/12)

Oxidative Cyclization of Trifluoroacetimidohydrazides with D-Glucose for the Metal-Free Synthesis of 3-Trifluoromethyl-1,2,4-Triazoles
A metal-free oxidative cyclization of readily available trifluoroacetimidohydrazides with D-glucose for the assembly of 3-trifluoromethyl-1,2,4-triazoles has been disclosed. D-glucose is applied as C1 synthon to provide methine source in the reaction. Control experiments have been conducted to shed light on the reaction mechanism. The synthetic utility of the protocol has been explored by the implementation of scale up reaction and the synthesis of the key skeleton of NKI-receptor ligand. (Figure presented.).
Lu, Shu-Ning,Yang, Hefei,Zhang, Jiajun,Chen, Zhengkai,Wu, Xiao-Feng
supporting information
p. 4982 - 4987
(2021/10/14)

Elemental Sulfur and Dimethyl Sulfoxide-Promoted Oxidative Cyclization of Trifluoroacetimidohydrazides with Methylhetarenes for the Synthesis of 3-Hetaryl-5-trifluoromethyl-1,2,4-triazoles
A metal-free approach for the synthesis of 3-hetaryl-5-trifluoromethyl-1,2,4-triazoles via sulfur/dimethyl sulfoxide-promoted oxidative cyclization of readily available trifluoroacetimidohydrazides with methylhetarenes has been developed. This transformation proceeds in cascade sulfur-mediated generation of thioaldehyde, condensation, intramolecular cyclization and oxidative aromatization sequence.
Chen, Zhengkai,Tang, Jianhua,Wu, Xiao-Feng,Zhang, Jiajun
supporting information
p. 3443 - 3447
(2021/11/10)

Direct Synthesis of β-Amino Aldehydes from Linear Allylic Esters Using O2as the Sole Oxidant
A tandem isomerization-anti-Markovnikov oxidation of linear allylic imidic esters is developed using bis(benzonitrile)palladium chloride as the catalyst and O2 as the sole oxidant, regiospecifically giving β-amino aldehydes as the product. tert-Butyl nitrite works as a simple, and the only, redox cocatalyst. tBuOH proves to be a crucial solvent for achieving excellent yield and specificity toward anti-Markovnikov aldehyde products.
Lei, Shu-Hui,Zhong, Ya,Cai, Xian-Peng,Huang, Qing,Qu, Jian-Ping,Kang, Yan-Biao
supporting information
p. 9273 - 9276
(2021/12/06)

α-Selective glycosylations using glycosyl: N-(ortho-methoxyphenyl)trifluoroacetimidates
Six N-(o-methoxyphenyl)trifluoroacetimidate glycosyl donors have been synthesized and their role as glycosyl donors has been investigated. The donors were synthesized with complete -selectivity, except in one case, and were found to be stable. When Bi(OTf
Kowalska, Karolina,Pedersen, Christian Marcus
supporting information
p. 1918 - 1925
(2020/03/23)

Palladium-Catalyzed Four-Component Carbonylative Cyclization Reaction of Trifluoroacetimidoyl Chlorides, Propargyl Amines, and Diaryliodonium Salts: Access to Trifluoromethyl-Containing Trisubstituted Imidazoles
A palladium-catalyzed four-component carbonylative cyclization reaction for the expeditious construction of trifluoromethyl-containing trisubstituted imidazoles has been achieved. With readily accessible trifluoroacetimidoyl chlorides, propargyl amines, a
Chen, Zhengkai,Wang, Wei-Feng,Yang, Hefei,Wu, Xiao-Feng
supporting information
p. 1980 - 1984
(2020/03/04)

FeCl3-Mediated Synthesis of 2-(Trifluoromethyl)quinazolin-4(3 H)-ones from Isatins and Trifluoroacetimidoyl Chlorides
An FeCl3-mediated cascade coupling/decarbonylative annulation reaction for the efficient construction of 2-(trifluoromethyl)quinazolin-4(3H)-ones has been developed. This transformation employs readily available isatins and trifluoroacetimidoyl chlorides as the starting materials, providing a facile and practical route to diverse biologically relevant quinazolin-4(3H)-one derivatives. A plausible reaction pathway has been proposed based on the mechanistic observations.
Wang, Le-Cheng,Du, Shiying,Chen, Zhengkai,Wu, Xiao-Feng
supporting information
p. 5567 - 5571
(2020/07/14)

A Convenient FeCl3-Mediated Synthesis of 5-Trifluoromethyl-1,2,4-triazoles from Trifluoroacetimidoyl Chlorides and Hydrazides
A low cost FeCl3-mediated cascade annulation of trifluoroacetimidoyl chlorides and hydrazides for the efficient synthesis of 5-trifluoromethyl-1,2,4-triazoles has been developed. The transformation proceeds through a cascade base-promoted intermolecular C?N bond formation and FeCl3-mediated intramolecular dehydration sequence under mild conditions. The protocol exhibits many notable features and can be readily scaled up to gram scale. (Figure presented.).
Du, Shiying,Wang, Le-Cheng,Yang, Zuguang,Chen, Zhengkai,Wu, Xiao-Feng
supporting information
p. 5130 - 5134
(2020/10/06)

Hydrogen-Borrowing Amination of Secondary Alcohols Promoted by a (Cyclopentadienone)iron Complex
Thanks to a highly active catalyst, the scope of the (cyclopentadienone)iron complex-promoted 'hydrogen-borrowing' (HB) amination has been expanded to secondary alcohols, which had previously been reported to react only in the presence of large amounts of co-catalysts. A range of cyclic and acyclic secondary alcohols were reacted with aromatic and aliphatic amines giving fair to excellent yields of the substitution products. The catalyst was also able to promote the cyclization of diols bearing a secondary alcohol group with primary amines to generate saturated N-heterocycles.
Aiolfi, Francesco,Bai, Xishan,Cettolin, Mattia,Dal Corso, Alberto,Gennari, Cesare,Piarulli, Umberto,Pignataro, Luca
supporting information
p. 3545 - 3555
(2019/09/09)

A simple synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and N-aryltrifluoroacetimidoyl chlorides
[Figure not available: see fulltext.] A novel synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and trifluoromethylated imidoyl chlorides in acetonitrile as solvent at room temperature without any catalyst is described. The FT-IR, 1H, 13C, 19F NMR spectral and elemental analysis confirm the structures of products. The synthesized azomethine ylides are easily purified by washing with diethyl ether and are stable even at high temperature. Heating of these ylides in refluxing acetonitrile, ethanol, or DMSO did not result in the intramolecular cyclization to imidazopyridine derivatives and only starting ylides were isolated.
Talebizadeh, Mahdiyeh,Anary-Abbasinejad, Mohammad,Darekordi, Ali
p. 235 - 239
(2019/05/15)

Preparation of Trifluoromethylated (Arylaminomethylene)malononitriles Suitable for Synthesis of 4-Amino-2-(trifluoromethyl) quinoline Derivatives by Intramolecular Friedel-Crafts Reaction
An approach for the synthesis of 4-amino-2-(trifluoromethyl)quinolines via the intramolecular Friedel-Crafts reaction of 2-(1-(arylamino)-2,2,2-trifluoroethylidene)malononitrile derivatives is reported. This simple protocol provides a wide variety of 4-am
Rahmani, Fariba,Darehkordi, Ali
p. 2124 - 2130
(2018/04/05)

Expeditious Synthesis of 6-Fluoroalkyl-Phenanthridines via Palladium-Catalyzed Norbornene-Mediated Dehydrogenative Annulation
A novel palladium-catalyzed, norbornene-mediated intermolecular dehydrogenative annulation approach for the synthesis of 6-fluoroalkyl-phenanthridines from aryl iodides and fluorinated imidoyl chlorides, which are important structural motifs for bioactive molecules, is reported. Fluorinated imidoyl chlorides served as a new type of electrophilic reagent in the Catellani-type reaction, which, in turn, could be readily prepared from various anilines and fluorinated carboxylic acids. Control experiments were carried out to study the mechanism of the reaction. This transformation is scalable and tolerates a broad range of functional groups.
Wang, Zhuo,Li, Tongyu,Zhao, Jinghui,Shi, Xiaonan,Jiao, Dequan,Zheng, Han,Chen, Chen,Zhu, Bolin
supporting information
p. 6640 - 6645
(2018/10/25)

PROCESS FOR THE PREPARATION OF 4-AMINO-5-FLUORO-3-CHLORO-6-(SUBSTITUTED)PICOLINATES
4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a 3,3-dialkoxyprop-1-yne and a substituted methylene amine by a series of steps.
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Paragraph 0059; 0060

(2014/06/25)

PROCESS FOR THE PREPARATION OF 4-AMINO-5-FLUORO-3-CHLORO-6-(SUBSTITUTED)PICOLINATES
4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a C1-C4 alkyl propiolate and a substituted methylene amine by a series of steps.
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Paragraph 0047; 0048

(2014/06/25)

4-CF3-ezetimibe analogs: Design, synthesis, and biological evaluation of cholesterol absorption inhibitions
On the purpose of looking for better cholesterol absorption inhibitors, several trifluoromethyl substituted ezetimibe analogs 1a-d were designed and synthesized. The key steps in the synthesis of these optically pure trans-4-CF3-β-lactams inclu
Liu, Yingle,Chen, Jun-Ling,Wang, Gai-Hong,Sun, Peng,Huang, Heyao,Qing, Feng-Ling
p. 5541 - 5543
(2013/09/23)

The asymmetric aza-claisen rearrangement: development of widely applicable pentaphenylferrocenyl palladacycle catalysts
Systematic studies have been performed to develop highly efficient catalysts for the asymmetric aza-Claisen rearrangement of trihaloacetimidates. Herein, we describe the stepwise development of these catalyst systems involving four different catalyst generations finally resulting in the development of a planar chiral pentaphenylferrocenyl oxazoline palladacycle. This complex is more reactive and has a broader substrate tolerance than all previously known catalyst systems for asymmetric aza-Claisen rearrange-ments. Our investigations also reveal that subtle changes can have a big impact on the activity. With the enhanced catalyst activity, the asymmetric aza-Claisen rearrangement has a very broad scope: the methodology not only allows the formation of highly enantioenriched primary allylic amines, but also secondary and tertiary amines; al-lylic amines with N-substituted quaternary stereocenters are conveniently accessible as well. The reaction conditions tolerate many important functional groups, thus providing stereoselective access to valuable functionalized building blocks, for example, for the synthesis of unnatural amino acids. Our results suggest that face-selective olefin coordination is the enantioselectivitydetermining step, which is almost exclusively controlled by the element of planar chirality.
Fischer, Daniel F.,Barakat, Assem,Xin, Zhuo-Qun,Weiss, Matthias E.,Peters, Rene
supporting information; experimental part
p. 8722 - 8741
(2010/03/31)

Facile preparation of polyfluoroalkylated aldimines from polyfluoroalkanoic acids
Polyfluoroalkylated aldimines were prepared by reducing polyfluoroalkyl imidoyl chlorides, which are readily available from polyfluoroalkanoic acids, with LTBA (lithium tri-tert-butoxyaluminum hydride). Georg Thieme Verlag Stuttgart.
Takagi, Jun,Takihana, Ryozo,Kuwano, Akiko,Uneyama, Kenji
p. 1624 - 1628
(2008/02/05)

PROCESS FOR PRODUCTION OF 1-ARYL-5-(TRIFLUOROMETHYL)-1H- TETRAZOLES
The present invention relates to a process for producing an N-aryl-2,2,2-trifluoroacetimidoyl chloride represented by Formula (2): the process comprising the step of reacting in an organic solvent a tertiary amine, a 2,2,2-trifluoro-N-arylacetamide repre
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Page/Page column 7

(2008/06/13)

Catalytic asymmetric synthesis of chiral allylic amines. Evaluation of ferrocenyloxazoline palladacycle catalysts and imidate motifs
(Chemical Equation Presented) Palladium(II) catalysts based on a ferrocenyloxazoline palladacyclic (FOP) scaffold were synthesized and evaluated for the rearrangement of prochiral allylic N-(4-methoxyphenyl)benzimidates. When iodide-bridged dimer FOP precatalysts are activated by reaction with excess silver trifluoroacetate, the allylic rearrangement of both E and Z prochiral primary allylic N-(4-methoxyphenyl)-benzimidates takes place at room temperature to give the corresponding chiral allylic N-(4-methoxyphenyl)benzamides in high yield and good ee (typically 81-95%). Several allylic imidate motifs were evaluated also. Because the corresponding enantioenriched allylic amide products can be deprotected in good yield to give enantioenriched allylic amines, allylic N-aryltrifiuoroacetimidates were identified as promising substrates.
Anderson, Carolyn E.,Donde, Yariv,Douglas, Christopher J.,Overman, Larry E.
p. 648 - 657
(2007/10/03)

Palladium-catalyzed tert-butoxycarbonylation of trifluoroacetimidoyl iodides
A modification and details of the palladium-catalyzed tert-butoxycarbonylation of 2,2,2-trifluoroacetimidoyl iodides 1, which gave the iminocarboxylates 2, one of the promising precursors to fluorinated α-amino acids, are described. The Pd-catalyzed carbonylation reaction was remarkably promoted by the use of DMF or DMI as an additive, enough to achieve the selective formation of tert-butyl iminoesters. Nucleophilic alkylation of the imine moiety of 2 and subsequent removal of N- and O-protecting groups gave a variety of 2-substituted 2-amino-3,3,3-trifluoropropanoic acid derivatives 3 in high yields.
Amii, Hideki,Kishikawa, Yosuke,Kageyama, Katsuhiko,Uneyama, Kenji
p. 3404 - 3408
(2007/10/03)

Generation and Reactions of Trifluoroacetimidoyl Radicals
N-Aryltrifluoroacetimidoyl radicals have been generated by three different methods: the tin-radical promoted deiodination and photochemical homolysis of imidoyl iodides and the thermal homolysis of imidoyl azo-compounds.N-trifluoroace
Dan-oh, Yasufumi,Matta, Hirokazu,Uemura, Junko,Watanabe, Hisayuki,Uneyama, Kenji
p. 1497 - 1508
(2007/10/02)

One-Pot Synthesis of Trifluoroacetimidoyl Halides
Trifluoroacetimidoyl chlorides 1 were obtained in 80-90percent yields when a mixture of trifluoroacetic acid and a primary amine was heated in carbon tetrachloride in the presence of triphenylphosphine and triethylamine.The corresponding bromides 2 were o
Tamura, Kenji,Mizukami, Hiromichi,Maeda, Kazuhiro,Watanabe, Hisayuki,Uneyama, Kenji
p. 32 - 35
(2007/10/02)

Homologation of trifluoroacetimidoyl iodides by palladium-catalyzed carbonylation. An approach to α-amino perfluoroalkanoic acids
Homologation of trifluoroacetimidoyl iodides and the related perfluoro-compounds by palladium-catalyst under CO(1atm)-atmosphere in the presence of alcohols gives α-imino perfluoroalkanoates which are transformed to α-amino perfluoroalkanoic acids.
Watanabe,Hashizume,Uneyama
p. 4333 - 4336
(2007/10/02)