56074-58-9Relevant articles and documents
Palladium-catalyzed denitrative α-arylation of ketones with nitroarenes
Li, Zhirong,Peng, Yonggang,Wu, Tao
supporting information, (2021/02/16)
The palladium-catalyzed α-arylation of ketones with readily available nitroarenes and nitroheteroarenes provides access to useful α-aryl and α-heteroaryl ketones. The use of the Pd/ BrettPhos catalysts was critical to achieve high efficiency for these transformations, whereas other catalysts led to decreased yields or no conversions. The intramolecular type substrate was also applied in this methodology and gave a chromone derivative. Polyaromatic carbonyl compounds can be easily obtained by multicomponent tandem reactions, via nucleophilic aromatic substitution (SNAr) or cross-coupling reaction followed by this denitrative arylation. Kinetic experiments show that the electronic effect of nitrobenzenes has a greater effect on the reaction rate than the electronic effect of ketones.
Facile one-pot palladium-catalyzed sequential coupling to diarylmethanes by using aryl methyl ketones as the methylene donors
Wang, Xing,Liu, Lian-Hua,Shi, Jin-Hua,Peng, Ji,Tu, Hai-Yang,Zhang, Ai-Dong
, p. 6870 - 6877 (2013/11/06)
A novel palladium-catalyzed coupling reaction of an aryl methyl ketone with two molecules of an aryl halide to yield symmetric diarylmethanes is described. In the facile one-pot reaction, the aryl methyl ketone acts as a formal methylene donor. The experimental facts, including TLC monitoring, speculated intermediates as the raw materials, analysis of the cesium benzoate coproduct by ex situ IR spectroscopy, and the cross-coupling reactions of two different aryl halides, indicate a mechanism involving a palladium-catalyzed sequential two-step coupling process, in which the presence of a trace amount of H 2O is indispensable. The reaction is applicable to a broad spectrum of substrates and delivers the products in good to excellent yields. Access to unsymmetrical diarylmethanes with this method is also explored and various factors are discussed. An aryl methyl ketone is used as the methylene donor to couple with two molecules of an aryl halide for the synthesis of various symmetric diarylmethanes under palladium catalysis. The mechanism involves a two-step coupling process in which the presence of a trace amount of H 2O is indispensable. The cross-coupling to unsymmetrical diarylmethanes with this method is also explored. Copyright
Palladium-catalyzed synthesis of diarylmethanes: Exploitation of carbanionic leaving groups
Schmink, Jason R.,Leadbeater, Nicholas E.
scheme or table, 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