- Palladium-Catalyzed Carboxylation of Vinyl Triflates. Electrosynthesis of α, β-Unsaturated Carboxylic Acids
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The electrocarboxylation of vinyl triflates performed with carbon dioxide and a catalytic amount of PdCl2(PPh3)2 affords α,β-unsaiurated carboxylic acids. The reactivity of vinyl triflates has been reversed in the presence of an electron source, since they now react with electrophiles. The reaction proceeds by an activation of the C-O bond of the vinyl triflate by a palladium(O) complex followed by an activation by electron transfer, of the vinylpalladium(II) complex formed in the oxidative addition.
- Jutand, Anny,Négri, Serge
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- Carboxylation of Alkenyl Boronic Acids and Alkenyl Boronic Acid Pinacol Esters with CO2 Catalyzed by Cuprous Halide
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A cuprous halide catalysed carboxylation of alkenyl boronic acids and alkenyl boronic acid pinacol esters under CO2, affording the corresponding α, β-unsaturated carboxylic acids in good yield, has been developed. The potassium (E)-trifluoro(styryl)borate is also compatible with this reaction. This simple and efficient copper(I) catalytic system showed good functional group tolerance.
- Hong, Junting,Nayal, Onkar S.,Mo, Fanyang
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supporting information
p. 2813 - 2818
(2020/05/16)
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- Method for preparing alpha, beta-unsaturated carboxylic acid by reacting alkenyl boron compound with carbon dioxide under catalysis of cuprous halide
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The invention discloses a method for preparing alpha, beta-unsaturated carboxylic acid through a carboxylation reaction of an alkenyl boron compound and carbon dioxide under the catalysis of cuprous halide. According to the method, carbon dioxide is used as a C1 source, the cuprous halide is adopted for catalysis, and alkoxide serves as alkali to react in an organic solvent, so the method is simple and easy to implement, has a wide substrate application range, converts various alkenyl boron compounds such as alkenyl boric acid, alkenyl borate and borate into corresponding alpha, beta-unsaturated carboxylic acid under mild conditions, and has a very high yield. The obtained product alpha, beta-unsaturated carboxylic acid is an important intermediate for preparing fine chemical products suchas perfumes, insecticides and the like.
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Paragraph 0071-0072
(2020/06/17)
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- Cobalt-catalyzed carboxylation of aryl and vinyl chlorides with CO2
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The transition-metal-catalyzed carboxylation of aryl and vinyl chlorides with CO2 is rarely studied, and has been achieved only with a Ni catalyst or combination of palladium and photoredox. In this work, the cobalt-catalyzed carboxylation of aryl and vinyl chlorides and bromides with CO2 has been developed. These transformations proceed under mild conditions and exhibit a broad substrate scope, affording the corresponding carboxylic acids in good to high yields.
- Wang, Yanwei,Jiang, Xiaomei,Wang, Baiquan
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supporting information
p. 14416 - 14419
(2020/12/01)
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- Palladium-Catalyzed Visible-Light-Driven Carboxylation of Aryl and Alkenyl Triflates by Using Photoredox Catalysts
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A visible-light-driven carboxylation of aryl and alkenyl triflates with CO2 is developed by using a combination of Pd and photoredox catalysts. This reaction proceeds under mild conditions and can be applied to a wide range of substrates including acyclic alkenyl triflates.
- Shimomaki, Katsuya,Nakajima, Tomoya,Caner, Joaquim,Toriumi, Naoyuki,Iwasawa, Nobuharu
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supporting information
p. 4486 - 4489
(2019/06/24)
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- Cobalt- and Nickel-Catalyzed Carboxylation of Alkenyl and Sterically Hindered Aryl Triflates Utilizing CO2
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A highly efficient cobalt-catalyzed reductive carboxylation reaction of alkenyl trifluoromethanesulfonates (triflates) has been developed. By employing Mn powder as a reducing reagent under 1 atm pressure of CO2 at room temperature, diverse alkenyl triflates can be converted to the corresponding α,β-unsaturated carboxylic acids. Moreover, the carboxylation of sterically hindered aryl triflates proceeds smoothly in the presence of a nickel or cobalt catalyst.
- Nogi, Keisuke,Fujihara, Tetsuaki,Terao, Jun,Tsuji, Yasushi
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p. 11618 - 11623
(2015/12/01)
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- Nickel-catalyzed carboxylation of aryl and vinyl chlorides employing carbon dioxide
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Nickel-catalyzed carboxylation of aryl and vinyl chlorides employing carbon dioxide has been developed. The reactions proceeded under a CO2 pressure of 1 atm at room temperature in the presence of nickel catalysts and Mn powder as a reducing agent. Various aryl chlorides could be converted to the corresponding carboxylic acid in good to high yields. Furthermore, vinyl chlorides were successfully carboxylated with CO2. Mechanistic study suggests that Ni(I) species is involved in the catalytic cycle.
- Fujihara, Tetsuaki,Nogi, Keisuke,Xu, Tinghua,Terao, Jun,Tsuji, Yasushi
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p. 9106 - 9109
(2012/07/13)
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- Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids
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A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst.
- Vitnik, Vesna D.,Milenkovi, Marina T.,Dilber, Sanda P.,Vitnik, Zeljko J.,Juranic, Ivan O.
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scheme or table
p. 741 - 750
(2012/10/07)
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- One-step conversion of ketones to conjugated acids using bromoform
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Phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent result in the formation of ,-unsaturated carboxylic acids. The reaction was performed at room temperature for 24h. The corresponding conj
- Vitnik,Ivanovic,Vitnik,Orevic,Zizak,Juranic,Juranic
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experimental part
p. 1457 - 1471
(2009/09/26)
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- First structure-activity relationship study on dopamine D3 receptor agents with N-[4-(4-Arylpiperazin-1-yl)butyl]-arylcarboxamide structure
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Structure-affinity relationships of N-[4-(4-arylpiperazin-1-yl)butyl] arylcarboxamides as D3 receptor ligands have been well characterized but not structure-activity relationships. In a first attempt to clarify this issue, seven 1-(2,3-dichloro
- Leopoldo, Marcello,Lacivita, Enza,Colabufo, Nicola A.,Contino, Marialessandra,Berardi, Francesco,Perrone, Roberto
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p. 7919 - 7922
(2007/10/03)
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- Activation of aryl and vinyl triflates by palladium and electron transfer - Electrosynthesis of aromatic and αβ-unsaturated carboxylic acids from carbon dioxide
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The electrochemical reduction of aryl and vinyl triflates in the presence of CO2 and a catalytic amount of palladium results in the formation of aromatic and αβ-unsaturated carboxylic acids. Aryl and vinyl triflates usually undergo palladium-catalysed cross-coupling reactions with nucleophiles. Their reactivity has been reversed in the presence of an electron source, so that they react with electrophiles such as CO2. The reaction proceeds through an activation of the C-O bond of the aryl or vinyl triflate by oxidative addition to a palladium(0) complex, followed by an activation by electron transfer of the thus formed aryl- or vinylpalladium(II) complexes.
- Jutand, Anny,Négri, Serge
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p. 1811 - 1821
(2007/10/03)
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- Palladium-Catalysed Hydroxycarbonylation of Vinyl and Aryl Triflates: Synthesis of α,β-Unsaturated and Aromatic Carboxylic Acids
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The palladium-catalysed hydroxycarbonylation of vinyl and aryl triflates, under a CO balloon, in the presence of potassium acetate affords α,β-unsaturated and aromatic carboxylic acids with one more carbon in good to high yield.The nature of the solvent and of the ligand have been proved to be crucial for the success of the reaction.Vinyl triflates undergo the hydroxycarbonylation at room temperature in DMF in the presence of Pd(OAc)2(PPh3)2.Aryl triflates produce best results at 60 deg C in DMSO in the presence of Pd(OAc)2 and 1,1-bis(diphenylphosphino)ferrocene (dppf).
- Cacchi, Sandro,Lupi, Alessandro
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p. 3939 - 3942
(2007/10/02)
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