- Copper-mediated trifluoromethylation using phenyl trifluoromethyl sulfoxide
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A new method for the generation of trifluoromethylcopper ( CuCF3 ) species from readily available phenyl trifluoromethyl sulfoxide has been developed. The CuCF3 reagent can be applied in efficient trifluoromethylations of aryl iodides and activated aryl bromides in the absence of additional ligands. Furthermore, the CuCF3 species can also undergo oxidative cross-coupling with terminal alkynes and arylboronic acids.
- Li, Xinjin,Zhao, Jingwei,Zhang, Liang,Hu, Mingyou,Wang, Limin,Hu, Jinbo
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supporting information
p. 298 - 301
(2015/03/04)
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- An "ortho effect" in electrophilic aromatic nitrations: Theoretical analysis and experimental validation
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Usually, a π-donor substituent acts as an ortho/para directing group in an electrophilic aromatic substitution reaction, and a π-acceptor substituent acts as a meta directing group. Interestingly, when a π-acceptor substituent is meta to a π-donor substituent, certain electrophilic aromatic nitration occurs ortho to the π-acceptor substituent rather than para . The "ortho effect", highlighted in various textbooks, has been tentatively analyzed here based on ab initio calculations. The reliability of the calculations was verified by the corresponding experimental data, including a newly-designed electrophilic aromatic nitration that also gave reasonable product distributions.
- Li, Hui-Jing,Wu, Yan-Chao,Dai, Jian-Hong,Song, Yan,Cheng, Runjiao,Qiao, Yuanyuan
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p. 1307 - 1312
(2015/02/05)
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- A novel catalytic process for trifluoromethylation of bromoaromatic compounds
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The palladium-catalyzed trifluoromethylation of aryl bromides has been achieved in micellar media. The micellar conditions result in enhanced yields and are applicable to bromoaromatics with ketone, aldehyde, hydroxyl and amine functionalities.
- Samant, Bhupesh S.,Kabalka, George W.
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supporting information; experimental part
p. 7236 - 7238
(2011/08/22)
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- The palladium-catalyzed trifluoromethylation of aryl chlorides
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The trifluoromethyl group can dramatically influence the properties of organic molecules, thereby increasing their applicability as pharmaceuticals, agrochemicals, or building blocks for organic materials. Despite the importance of this substituent no general method exists for its installment onto functionalized aromatic substrates. Current methods either require the use of harsh reaction conditions or suffer from a limited substrate scope. Here we report the palladium-catalyzed trifluoromethylation of aryl chlorides under mild conditions, allowing the transformation of a wide range of substrates, including heterocycles, in excellent yields. The process tolerates functional groups such as esters, amides, ethers, acetals, nitriles, and tertiary amines and, therefore, should be applicable to late-stage modifications of advanced intermediates. We have also prepared all the putative intermediates in the catalytic cycle and demonstrated their viability in the process.
- Cho, Eun Jin,Senecal, Todd D.,Kinzel, Tom,Zhang, Yong,Watson, Donald A.,Buchwald, Stephen L.
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scheme or table
p. 1679 - 1681
(2011/08/10)
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- Substituted diphenyl ethers
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A compound of the formula: STR1 and salts and esters thereof, useful as intermediates for the preparation of compounds of the formula STR2 wherein R1 is an alkyl group optionally substituted by one or more fluorine atoms or by an optionally substituted phenyl group R2 is No2 or Cl and R6 is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms.
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- Trifluoromethyl substituted 1-aminoindanes
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4(5 or 6 or 7)-Trifluoromethyl-1-aminoindanes, useful as inhibitors of N-methyl transferase.
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