- Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C-H activation
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Carbyne, an interesting synthetic intermediate, has recently been generated from hypervalent iodine precursors via photoredox catalysis. Given the underexplored chemistry of carbyne, due to the paucity of carbyne sources, we are intrigued to discover a new source for this reactive species from classical reagents-phosphonium ylides. Our novel strategy employing phosphonium ylides in an olefin hydrocarbonation reaction features a facile approach for constructing carbon-carbon bonds through metal-free and benign reaction conditions. Moreover, the hydrocarbonation products were delivered in a highly regioselective manner.
- Das, Mrinmoy,Vu, Minh Duy,Zhang, Qi,Liu, Xue-Wei
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- From Alkyl Halides to Ketones: Nickel-Catalyzed Reductive Carbonylation Utilizing Ethyl Chloroformate as the Carbonyl Source
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Ketones are an important class of molecules in synthetic and medicinal chemistry. Rapid and modular synthesis of ketones remains in high demand. Described here is a nickel-catalyzed three-component reductive carbonylation method for the synthesis of dialkyl ketones. A wide range of both symmetric and asymmetric dialkyl ketones can be accessed from alkyl halides and a safe CO source, ethyl chloroformate. The approach offers complementary substrate scope to existing carbonylation methods while avoiding the use of either toxic CO or metal carbonyl reagents.
- Shi, Renyi,Hu, Xile
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supporting information
p. 7454 - 7458
(2019/04/30)
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- Dual Functionalization of α-Monoboryl Carbanions through Deoxygenative Enolization with Carboxylic Acids
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A dual functionalization of 1,1-diborylalkanes through deoxygenative enolization with carboxylic acids was developed. 1,1-Diborylalkanes were activated by MeLi to generate α-monoboryl carbanions. In situ IR spectroscopy indicated an interaction between carboxylic acid and 1,1-diborylalkane before addition of the activation reagent. Release of the active α-monoboryl carbanion from the masked form was necessary for its reaction with carboxylate to afford enolate species. Electrophilic trapping of enolate species with various electrophiles achieved dual functionalization of 1,1-diborylalkanes to afford a variety of α-mono, di-, and tri-substituted ketones.
- Sun, Wei,Wang, Lu,Xia, Chungu,Liu, Chao
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supporting information
p. 5501 - 5505
(2018/04/09)
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- A preparation method of the organic compound (by machine translation)
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The invention relates to a preparation method of the organic compound: comprising the following steps: step one: in the nitrogen atmosphere, are added to the organic solvent in the organic carboxylic acid compound with the [...] compound; step two: to a mixture obtained in the step of adding alkyl lithium reagent, after reaction, is restored to the room temperature; step three: step b by heating the reaction mixture; step four: to step three by the electrophilic reagent is added in the mixture, to continue to reaction to obtain the ketone compound; wherein the organic carboxylic acid compound, alkyl lithium reagent, [...] compound and electrophilic reagents of the amount-of-substance ratio of 1.0: 2.5: 1.5: (1.0 - 2.0). The invention in a simple, economic, easy to obtain the raw material of the substrate, with only the addition of alkyl lithium as the activating agent, does not need any catalyst, a step to construct the previous method is difficult to efficient implementation of the ketone compound compound, such compound in the medical synthetic intermediates and organic photoelectric material science in very great application prospect. (by machine translation)
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Paragraph 0135; 0139
(2018/09/08)
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- One-pot synthesis of ketones using N-methoxy-N-methyl-2-pyridyl urethane
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The one-pot reaction of N-methoxy-N-methyl-2-pyridyl urethane with Grignard and organolithium reagents provided an efficient method for the preparation of unsymmetrical ketones.
- Lee, Na Ra,Lee, Jae In
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p. 1249 - 1255
(2007/10/03)
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- Synthese de tertiobutylcetones α-azotees de type =N-C(R1)(R2)-CO-C(CH3)3
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The α-nitrogen-ketones 2, 3 and 4 were prepared from α-bromoketones.These were synthesized by the bromination of the ketones which had been obtained by the pinacolone or benzyltertiobutylketone alkylation from the corresponding halo-derivatives.We have observed that the bromination of the ketones depends to some extent upon the nature of these compounds.
- Montignoul, Claude,Richard, Marie-Josee,Vigne, Christian,Giral, Louis
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p. 1509 - 1519
(2007/10/02)
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