55681-26-0Relevant academic research and scientific papers
Aqueous α-Arylation of Mono- and Diarylethanone Enolates at Low Catalyst Loading
Astarloa, Iratxe,SanMartin, Raul,Herrero, María Teresa,Domínguez, Esther
supporting information, p. 1711 - 1718 (2018/03/21)
Acetophenone and deoxybenzoin derivatives are selectively α-arylated using a combination of very small amounts of palladium acetate and diphenylphosphine oxide as catalyst system and water as the only solvent. Target di- and triarylethanones are isolated virtually free of metal residues, and the reaction is amenable to gram-scale. A mechanistic proposal based on TEM images, poisoning experiments, kinetic plot and ESI-MS spectrometry is also provided. (Figure presented.).
One-pot synthesis of diarylmethanones through palladium-catalyzed sequential coupling and aerobic oxidation of aryl bromides with acetophenone as a latent carbonyl donor
Wang, Xing,Liu, Fu-Di,Tu, Hai-Yang,Zhang, Ai-Dong
, p. 6554 - 6562 (2014/08/05)
A one-pot palladium-catalyzed synthesis of symmetrical and unsymmetrical diarylmethanones using acetophenone and aryl bromides as raw materials has been developed. In this reaction, acetophenone acts as a latent carbonyl donor and two pathways of palladium-catalyzed sequential coupling and aerobic oxidation are identified. The reaction is applicable to a spectrum of substrates and delivers the products in moderate to good yields. This method can be used for the synthesis of ketoprofen, a nonsteroidal anti-inflammatory drug, in a two-step procedure and 45% overall yield.
Aerobic dehydrogenative α-diarylation of benzyl ketones with aromatics through carbon-carbon bond cleavage
More, Nagnath Yadav,Jeganmohan, Masilamani
supporting information, p. 804 - 807 (2014/03/21)
Substituted benzyl ketones reacted with aromatics in the presence of K 2S2O8 in CF3COOH at room temperature, yielding α-diaryl benzyl ketones through a carbon-carbon bond cleavage. In the reaction, two new carbon-carbon bonds were formed and one carbon-carbon bond was cleaved. It is very interesting that two different nucleophiles such as benzyl ketones and aromatics were coupled together without metal, which is unusual in organic synthesis.
Lewis acid-promoted friedel-crafts alkylation reactions with α-ketophosphate electrophiles
Smith, Austin G.,Johnson, Jeffrey S.
supporting information; experimental part, p. 1784 - 1787 (2010/09/05)
The BF3·OEt2-promoted nucleophilic substitution of α-aryl-α-ketophosphates to afford α,α-diaryl ketone products is described. Electron-rich α-ketophosphates perform best, with electron-neutral and electron-poor substrates also tolerated. The reaction is tolerant of a range of aromatic, heteroaromatic, and nonaromatic nucleophiles, with yields ranging from 44% to 84%. Enantioenriched starting material yields racemic product, suggesting an SN1 pathway via an acylcarbenium ion.
Palladium-catalyzed synthesis of diarylmethanes: Exploitation of carbanionic leaving groups
Schmink, Jason R.,Leadbeater, Nicholas E.
supporting information; experimental part, p. 2575 - 2578 (2009/10/02)
A novel route to the synthesis of diarylmethanes via a Pd-catalyzed α-arylation of benzyl ketones is rseported. By harnessing the inherent reactivity of enolates, it is possible to circumvent the need for a transmetalating reagent such as boron for the co
A highly practical and general route for α-arylations of ketones using bis-phosphinoferrocene-based palladium catalysts
Grasa, Gabriela A.,Colacot, Thomas J.
, p. 522 - 529 (2013/01/03)
Well-defined, air-stable Pd complexes of bis-phosphinoferrocene family of catalysts have been studied in the arylation of various ketones with aryl chlorides and aryl bromides. Bis(di-tert-butyl)phosphinoferrocene (DtBPF)-based catalysts such as (DtBPF) P
Reductive cross-coupling between N-acylbenzimidazoles and diarylketones promoted by Sm/TiCl4
Du, Jingxing,Wang, Xiaoxia,Zheng, Renwei
, p. 14 - 15 (2007/10/03)
The reductive cross-coupling reaction between N-acylbenzimidazoles and diarylketones promoted by Sm/TiCl4 was performed in refluxing THF under a nitrogen atmosphere, to give 1,2,2-triaryl ethanones in moderate to good yields.
α-arylation of ketones using highly active, air-stable (DtBPF)PdX2 (X = Cl, Br) catalysts
Grasa, Gabriela A.,Colacot, Thomas J.
, p. 5489 - 5492 (2008/09/19)
α-Arylation of various ketones with aryl chlorides and bromides using the well-defined and air-stable (DtBPF)PdX2 (X = Cl, Br) catalysts gave 80-100% yield of the coupled products under relatively mild conditions at low catalyst loadings. The X
PCP-Bis(phosphinite) pincer complexes: new homogeneous catalysts for α-arylation of ketones
Churruca, Fátima,SanMartin, Raul,Tellitu, Imanol,Domínguez, Esther
, p. 3233 - 3237 (2007/10/03)
Two new p-alkoxycarbonylated palladium bis(phosphinite) PCP pincer complexes are easily prepared and for the first time evaluated as homogeneous catalysts in α-arylation of ketone enolates. Apart from the total absence of phenyl-aryl exchange by-products and significantly low catalyst loadings, the general α-arylation protocols described in this letter feature not only a broad applicability to a range of ketones and aryl bromides with marked electronic and steric differences but also the possibility to generate mono-diarylated products.
