- Iron-Catalyzed Halogen Exchange of Trifluoromethyl Arenes**
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The facile production of ArCF2X and ArCX3 from ArCF3 using catalytic iron(III)halides is reported, which constitutes the first iron-catalyzed halogen exchange for non-aromatic C?F bonds. Theoretical calculations suggest direct activation of C?F bonds by iron coordination. ArCX3 and ArCF2X products of the reaction are synthetically valuable due to their diversification potential. In particular, chloro- and bromodifluoromethyl arenes (ArCF2Cl, ArCF2Br respectively) provide access to a myriad of difluoromethyl arene derivatives (ArCF2R). To optimize for mono-halogen exchange, a statistical method called Design of Experiments was used. Optimized parameters were successfully applied to electron rich and electron deficient aromatic substrates, and to the late stage diversification of flufenoxuron, a commercial insecticide. These methods are highly practical, being run at convenient temperatures and using inexpensive common reagents.
- Dorian, Andreas,Landgreen, Emily J.,Petras, Hayley R.,Shepherd, James J.,Williams, Florence J.
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supporting information
p. 10839 - 10843
(2021/06/21)
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- Niobium(v)-catalyzed defluorinative triallylation of α,α,α-trifluorotoluene derivatives by triple C-F bond activation
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The catalytic defluorinative triallylation of α,α,α-trifluorotoluene derivatives via C-F bond activation has been achieved by the use of the NbCl5 catalyst and allyltrimethylsilane as a nucleophile. Several control experiments have suggested the importance of the conjugation between the fluorine atoms and the carbocation center in this reaction.
- Saito, Kodai,Umi, Taishi,Yamada, Takayuki,Suga, Takuya,Akiyama, Takahiko
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supporting information
p. 1767 - 1770
(2017/03/09)
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- Chlorination and alkylation of toluene with carbon tetrachloride
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It was shown that benzyl chloride can be synthesized from toluene and carbon tetrachloride with a high selectivity. The optimum conditions of side-chain chlorination and benzene-ring alkylation in the CCl4-toluene system were determined.
- Smirnov,Nevskaya,Golubeva
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- Process for the preparation of trichloromethyl-substituted aromatic compounds, and trichloromethyl-substituted aromatic compounds obtained in this process
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Trichloromethyl-substituted aromatic compounds are obtained by the chlorination of thioethers of the formula STR1 wherein Ar represents an optionally substituted aryl radial, X1 denotes hydrogen or halogen, and R1 represents optionally substituted alkyl, aralkyl, the nitrile group, an optionally substituted aryl radical or the group STR2 wherein Ar and X have the meaning given. The compounds, of which some are new, can be used as intermediate products for plant protection agents.
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- Substituted Benzotrichloride Synthesis by Phase Transfer-Catalyzed Chlorination
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A new method for converting benzyl and benzal chlorides to benzotrichlorides is reported.In contrast to prior art, the process involves contacting the substrates with strong alkali in a two-phase system containing phase transfer catalyst using organic soluble perchloralkanes acting upon base-generated carbanions.The method is particularly useful for preparing benzotrichlorides substituted by either alkyl or nitro groups.
- Chupp, J. P.,Grabiak, R. C.,Leschinsky, K. L.,Neumann, T. L.
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p. 224 - 226
(2007/10/02)
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