- CATALYST-FREE AND REDOX-NEUTRAL INNATE TRIFLUOROMETHYLATION AND ALKYLATION OF (HETERO)AROMATICS ENABLED BY LIGHT
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The present disclosure relates to reagents and method for performing trifluoromethylation, difluoromethylation or alkylation of aromatic or heteroaromatic rings in a redox-neutral manner without any catalyst which are enabled by light. In addition, there are methods for synthesizing the starting reagents used in the trifluoromethylation, difluoromethylation or alkylation reactions.
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Page/Page column 16-17
(2019/04/26)
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- Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light
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The Minisci alkylation is useful to functionalize aromatics via alkyl radical addition. Current approaches to prepare alkyl radicals follow either oxidative or reductive pathways from various functional groups. Developing new strategy beyond these traditional methods remains elusive yet highly significant. In this article, we present a redox-neutral and catalyst-free protocol to engender alkyl radicals in the context of trifluoromethylation and general alkylation of arenes. This protocol, via the Norrish type I concept to produce alkyl radicals, accommodates various functional groups and delivers the product in good yields. This method identified a series of compounds as the trifluoromethylation and alkylation reagents assisted by light. It is expected that these compounds can find potential applications in other radical-involved reactions.
- Liu, Peng,Liu, Wenbo,Li, Chao-Jun
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supporting information
p. 14315 - 14321
(2017/10/17)
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- Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction
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We describe a simple, metal-and oxidant-free photochemical strategy for the direct trifluoromethylation of unactivated arenes and heteroarenes under either ultraviolet or visible light irradiation. We demonstrated that photoexcited aliphatic ketones, such as acetone and diacetyl, can be used as promising low-cost radical initiators to generate CF3 radicals from sodium triflinate efficiently. The broad utility of this strategy and its benefit to medicinal chemistry are demonstrated by the direct trifluoromethylation of unprotected bidentate chelating ligand, xanthine alkaloids, nucleosides, and related antiviral drug molecules.
- Li, Lu,Mu, Xiaoyue,Liu, Wenbo,Wang, Yichen,Mi, Zetian,Li, Chao-Jun
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supporting information
p. 5809 - 5812
(2016/06/09)
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- HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS AND COMBINATIONS THEREOF
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Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds and combinations of such compounds and other therapeutic agents.
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Page/Page column 104
(2015/07/07)
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- HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS
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Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds.
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Page/Page column 89
(2014/01/18)
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- SULPHUR-LINKED IMIDAZOLE COMPOUNDS FOR THE TREAMENT OF HIV
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This invention relates to isophthalonitrile derivatives of formula (I) or pharmaceutically acceptable salts, solvates or derivative thereof, wherein R1 to R3 are defined in the description, and to processes for the preparation thereof, intermediates used in their preparation of, compositions containing them and the uses of such derivatives.The compounds of the present invention bind to the enzyme reverse transcriptase and are modulators, especially inhibitors thereof.
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Page/Page column 52
(2010/02/14)
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- Photoinduced Electron-transfer Reaction of Difluorodiiodomethane with Azaaromatic Compounds and Enamines
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Irradiation of difluorodiiodomethane 1 with pyrroles, indole and imidazoles in dimethylformamide gives the corresponding trifluoromethylated products, whereas irradiation with enamines results in 2-trifluoromethyl ketones.A photoinduced electron-transfer mechanism is proposed.
- Chen, Qing-Yun,Li, Zhan-Ting
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p. 645 - 648
(2007/10/02)
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- Photochemical Perfluoroalkylation of Imidazoles
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Imidazole and its derivatives undergo facile trifluoromethylation or perfluoroalkylation, in methanol solution at ambient temperature, following radical dissociation of RFI by γ or UV irradiation.In the case of imidazole, attack occurs preferen
- Kimoto, Hiroshi,Fujii, Shozo,Cohen, Louis A.
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p. 2867 - 2872
(2007/10/02)
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- Trifluoromethylimidazoles and a method for their preparation
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4(5)-Trifluoromethylimidazoles having optional substituents in the 1 and 2 positions are provided. The novel 4(5)-trifluoromethylimidazoles are prepared by reacting a 1,1-dihalo-3,3,3-trifluoroacetone compound with an appropriate carboxaldehyde and ammoni
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- 2-Pyrazinyl-trifluoromethylimidazoles and a method for their preparation
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4(5)-Trifluoromethylimidazoles having optional substituents in the 1 and 2 positions are provided. The novel 4(5)-trifluoromethylimidazoles are prepared by reacting a 1,1-dihalo-3,3,3-trifluoroacetone compound with an appropriate carboxaldehyde and ammoni
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- 4-Trifluoromethylimidazoles and 5-(4-pyridyl)-1,2,4-triazoles, new classes of xanthine oxidase inhibitors.
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The syntheses of a number of 2-substituted 4-trifluoromethylimidazoles and 3-substituted 5-(4-pyridyl)-1,2,4-triazoles are described. The trifluoromethylimidazoles were prepared from 3,3-dibromo-1,1,1-trifluoroacetone after hydrolysis with aqueous sodium acetate solution and condensation with an aldehyde in the presence of ammonia. Basic hydrolysis of the trifluoromethyl group was found to provide a facile method for the synthesis of imidazole-4-carboxylic acids. In the imidazole series a 2-aryl substituent and a free imino group were required for xanthine oxidase inhibitory activity. The triazoles were obtained through the reaction of an aroylhydrazine and an imino ether followed by thermal ring closure of the intermediate acylamidrazone. As in the imidazole series, a free imino group is an absolute requirement for in vitro activity. Additional structure-activity relationships of these compounds are presented.
- Baldwin et al.
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