- Reactions of trichloromethanesulfonyl chloride and carbon tetrachloride with silyl enol ethers catalyzed by a ruthenium(II) phosphine complex
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The reactions of trichloromethanesulfonyl chloride with trimethylsilyl enol ethers of acetophenones in the presence of a ruthenium(II) phosphine complex gave 1-aryl-3,3-dichloropropen-1-one together with α-chloroacetophenones. The product ratio depended on the substituent on the aromatic ring of the silyl enol ether. The reactions of carbon tetrachloride with the silyl enol ethers under similar conditions afforded 1-aryl-3,3-dichloropropen-1-one in good yield.
- Kamigata, Nobumasa,Udodaira, Kumiko,Yoshikawa, Manabu,Shimizu, Toshio
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- Functionalized β,β-dichloroenones and β,β-dibromoenones as versatile building blocks: Synthesis and transformations
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An efficient one-step synthesis of functionalized β,β-dichloroenones and β,β-dibromoenones was achieved via the Fe-catalyzed radical induced reaction between silyl enol ethers and carbon tetrachloride, bromotrichloromethane or carbon tetrabromide in moderate to good yields. This reaction proceeds through addition of the trichloromethyl or tribromomethyl radical group to the C[dbnd]C bond of the silyl enol ethers and subsequent base-induced elimination under mild conditions.
- Li, Dengke
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supporting information
(2021/11/30)
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- Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride
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A novel reactivity of 1,1,1-trifluoroalkanones is reported, where the reaction with AlCl3 results in the formation of 1,1-dichloro-1-alkenones. The reaction scope was found to be broad, with various chain lengths and aryl substituents tolerated. For substrates containing an electron-rich aromatic ring, further reactions take place, resulting in bicyclic and/or rearrangement products.
- Lansbergen, Beatrice,Meister, Catherine S.,McLeod, Michael C.
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supporting information
p. 404 - 409
(2021/03/20)
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- Synthesis of poly-functionalized pyrazoles under Vilsmeier-Haack reaction conditions
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Synthesis of 1,3-disubstituted 5-chloro-1H-pyrazole-4-carbaldehydes was achieved by formylation of the corresponding 5-chloro-1H-pyrazoles under Vilsmeier-Haack conditions.
- Popov, Aleksandr V.,Kobelevskaya, Valentina A.,Larina, Ludmila I.,Rozentsveig, Igor B.
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- Enantioselective, catalytic trichloromethylation through visible-light-activated photoredox catalysis with a chiral iridium complex
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An enantioselective, catalytic trichloromethylation of 2-acyl imidazoles and 2-acylpyridines is reported. Several products are formed with enantiomeric excess of ≥99%. In this system, a chiral iridium complex serves a dual function, as a catalytically active chiral Lewis acid and simultaneously as a precursor for an in situ assembled visible-light-triggered photoredox catalyst.
- Huo, Haohua,Wang, Chuanyong,Harms, Klaus,Meggers, Eric
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supporting information
p. 9551 - 9554
(2015/08/18)
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- Synthesis of α-Functionalized Trichloromethylcarbinols
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A new series of α-functionalized trichloromethylcarbinols have been synthesized from corresponding α-halomethyl ketones, esters, and amides in 48-78% overall yields. Reactivity of nitrates obtained in the first step was dependent on the electron-withdrawi
- Ram, Ram N.,Soni, Vineet Kumar
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p. 8922 - 8928
(2015/09/15)
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- Electrophilic Reactions of Carbonyl Compounds and their Derivatives. VI. Vinyl Ethers and Chlorinated Hydrocarbons in the Synthesis of Pyrylium Salts
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Two- and three-component condensations of α-ethoxystyrene with carbonyl compounds and their derivatives serving as a source of heterocarbenium and hydroxyallyl cations are studied.The reactions result in formation of monocyclic pyrilium salts.
- Luk'yanov, S. M.
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p. 794 - 800
(2007/10/03)
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