![N-[2-(trifluoromethyl)phenyl]acetamide](/Databaselist/images/loading.webp)
88-17-5Relevant academic research and scientific papers
Cross-Coupling through Ag(I)/Ag(III) Redox Manifold
Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie
supporting information, p. 15396 - 15405 (2021/10/12)
In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.
A metal-free picolinamide assisted electrochemical ortho-trifluoromethylation of arylamines
Wang, Kai,Hou, Jiahao,Wei, Tingting,Zhang, Changjun,Bai, Renren,Xie, Yuanyuan
, (2020/12/21)
An eco-friendly and effective electrochemical process was developed for the ortho-trifluoromethylation of arylamines using CF3SO2Na as the trifluoromethyl source, affording the desired products in moderate to good yields with high regioselectivity under mild reaction conditions. Importantly, the requirement for both transition metals and oxidants utilized in previous methods were avoided. A radical mechanism was proposed on the basis of various control experiments.
Transition metal-free direct C–H trifluoromethyltion of (hetero)arenes with Togni's reagent
Chen, Xiaoyu,Ding, Licheng,Li, Linlin,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information, (2019/12/30)
A new transition-metal-free direct C–H trifluoromethylation reaction of (hetero)arenes with Togni's reagent was developed. This transformation proceeded smoothly under mild conditions and exhibited good tolerance of many synthetically relevant functional groups. It provided an alternative approach for the synthesis of trifluoromethylated (hetero)arenes.
o-aminotrifluorotoluene synthesis method
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Paragraph 0006; 0013-0021, (2020/01/25)
The invention discloses an o-aminotrifluorotoluene synthesis method, wherein trifluorotoluene is used as a raw material, and a target compound is obtained through two-step reaction of nitration and reduction. Compared with the method in the prior art, the method of the invention has the following characteristics that trifluorotoluene is used as the raw material, so that the source is wide, and thepreparation is convenient; the nitration reaction is carried out at a normal pressure and a low temperature, so that the corrosion of the material to the pipeline and the equipment is small, and thenitration reaction is safe and reliable to the environment and operators; and the cheap nickel catalyst is used for replacing the common noble metal catalysts such as palladium, platinum and the like,so that the production cost is reduced, the methanol as the solvent is convenient to recover and can be recycled, and the emission of organic matters in the production process is reduced.
Visible-light-induced Pd-catalyzed: Ortho -trifluoromethylation of acetanilides with CF3SO2Na under ambient conditions in the absence of an external photocatalyst
Zou, Long,Li, Pinhua,Wang, Bin,Wang, Lei
, p. 3737 - 3740 (2019/04/01)
A visible-light-induced Pd-catalyzed ortho-trifluoromethylation of acetanilides with CF3SO2Na was developed. The reaction proceeded smoothly at room temperature in air without any external photocatalyst or additive, providing the desired products in moderate to good yields with good functional group tolerance and regioselectivity.
Eco-friendly hydrogenation of aryl azides to primary amines on graphene oxide-decorated bimetallic Rh-Pt nanoparticles (RhPt@GO NPs)
Kilbas, Benan,Kara, Belguzar Yasemin
, p. 33 - 37 (2019/01/26)
Graphene oxide-supported rhodium/platinum (Rh-Pt) nanoparticles (Rh-Pt@GO NPs) are a promising catalyst for the reduction of aryl azides to primary amines. Rh-Pt@GO NPs have been produced by the microwave-assisted sonochemical method. This catalyst showed superior catalytic activity to afford quantitative yields of primary amines under an extremely mild condition in the presence of sodium borohydride. The synthesized novel catalyst was easily recovered by centrifugation and reused without loss of its catalytic activity. The spectroscopic analyses of the RhPt@GO NPs indicated the formation of highly crystalline, monodisperse, and colloidally stable RhPt@GO NPs.
Nickel-Catalyzed Direct C-H Trifluoromethylation of Free Anilines with Togni's Reagent
Gao, Xianying,Geng, Yang,Han, Shuaijun,Liang, Apeng,Li, Jingya,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie
supporting information, p. 3732 - 3735 (2018/07/22)
An efficient nickel-catalyzed C-H trifluoromethylation for the synthesis of trifluoromethylated free anilines using Togni's reagent has been developed. This approach exhibits a good functional group tolerance, good regioselectivity, and chemoselectivity under mild conditions. The newly developed economical one-step method is a better alternative to synthesize trifluoromethylated free anilines.
Preparation method of trifluoromethylamine
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Paragraph 0023-0026; 0027-0045; 0046-0056, (2018/09/28)
The invention relates to a preparation method of trifluoromethylamine. The method includes the following steps that aromatic amine shown in the formula (1) and a trifluoromethyl reagent shown in the formula (2) react in a solvent under the condition that an alkali and/or nickel compound exists, and the trifluoromethylamine compound shown in the formula (3) is generated. According to the preparation method of trifluoromethylamine, aromatic amine and 1-trifluoromethyl-1,2-iodobenzoyl-3(H)-ketone serve as raw materials and react under the condition that the alkali and/or nickel compound exists through the amino positioning effect on aromatic nucleus. The synthesis steps of the method are simple, the cost of the raw materials is low, the production cost of trifluoromethylamine can be greatly reduced, and large-scale industrialized production is promoted.
Iron-catalyzed: Ortho trifluoromethylation of anilines via picolinamide assisted photoinduced C-H functionalization
Xia, Chengcai,Wang, Kai,Wang, Guodong,Duan, Guiyun
, p. 2214 - 2218 (2018/04/05)
A convenient, oxidant-free protocol was developed for the ortho trifluoromethylation of aniline via picolinamide assisted Fe-promoted C-H functionalization under ultraviolet irradiation. In this transformation acetone essentially acted as both a solvent to dissolve reactants and a low-cost radical initiator to efficiently generate a CF3 radical from Langlois' reagent. A broad substrate scope was tolerated and picolinamide bearing strong electron withdrawing groups also could be transformed into the corresponding products with acceptable yields. Furthermore, the value of this method has been highlighted via the efficient synthesis of the nonsteroidal anti-inflammatory drug floctafenine.
Coordinating Activation Strategy-Induced Selective C?H Trifluoromethylation of Anilines
Xu, Jun,Cheng, Ke,Shen, Chao,Bai, Renren,Xie, Yuanyuan,Zhang, Pengfei
, p. 965 - 970 (2018/02/12)
A simple protocol for the synthesis of 2-(trifluoromethyl)aniline derivatives through a coordinating activation strategy was developed. The reaction showed good reactivity and gave the target products in moderate to good yields. Pleasingly, the directing group could be recovered in excellent yield. Furthermore, this strategy allowed efficient access to the synthesis of floctafenine. A single-electron-transfer mechanism was proposed to be responsible for this trifluoromethylation reaction.
