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.).
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.
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.
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.
