1039775-42-2Relevant academic research and scientific papers
A convenient and efficient C-OH bond activation, PdCl2(PPh3)2catalyzed, C-C bond formation of tautomerizable quinolinones with the aid of BOP reagent and boronic acids
Kumar, Yadavalli Suneel,Dasaradhan,Prabakaran, Kamalakannan,Nawaz Khan, Fazlur-Rahman,Jeong, Euh Duck,Chung, Eun Hyuk,Kim, Hyun Gyu
, p. 40259 - 40268 (2014)
An efficient, highly chemoselective PdCl2(PPh3)2catalyzed, C-C bond formation of tautomerizable quinolinones with various boronic acids via C-OH bond activation using benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (BOP) reagent in the presence of K2CO3/1,4-dioxane system under aqueous condition, leads to the formation of functionalized quinolines in excellent yields, which offers great utility advantages in the synthesis of interesting compounds. This journal is
Highly efficient suzuki-miyaura coupling of heterocyclic substrates through rational reaction design
Fleckenstein, Christoph A.,Plenio, Herbert
scheme or table, p. 4267 - 4279 (2009/05/07)
A dicyclohexyl(2-sulfo-9-(3-(4-sulfophenyl)propyl)-9H-fluoren-9-yl) phosphonium salt was synthesized in 64% overall yield in three steps from simple commercially available starting materials. The highly water-soluble catalyst obtained from the corresponding phosphine and [Na2PdCl4] enabled the Suzuki coupling of a broad variety of N- and S-heterocyclic substrates. Chloropyridines (-quinolines) and aryl chlorides were coupled with aryl-, pyridineor indoleboronic acids in quantitative yields in water/n-butanol solvent mixtures in the presence of 0.005-0.05 mol% of Pd catalyst at 100°C, chloropurines were quantitatively Suzuki coupled in the presence of 0.5 mol% of catalyst, and S-heterocyclic aryl chlorides and aryl- or 3-pyridylboronic acids required 0.01-0.05 mol % Pd catalyst for full conversion. The key to the high activity of the Pd-phosphine catalyst is the rational design of the reaction parameters (i.e., the presence of water in the reaction mixture, good solubility of reactants and catalyst in n-butanol/water (3:1), and the electron-rich and sterically demanding nature of the phosphine ligand).
