1039775-46-6Relevant academic research and scientific papers
Deprotonative metalation of aromatic compounds by using an amino-based lithium cuprate
Nguyen, Tan Tai,Marquise, Nada,Chevallier, Floris,Mongin, Florence
experimental part, p. 10405 - 10416 (2011/10/12)
Deprotonative cupration of aromatic compounds by using amino-based lithium cuprates was optimized with 2,4-dimethoxypyrimidine and 2-methoxypyridine as the substrates and benzoyl chloride as the electrophile. [(tmp)2CuLi] (+2 LiCl) (tmp=2,2,6,6-tetramethylpiperidino) was identified as the best reagent and its use was extended to anisole, 1,4-dimethoxybenzene, other substituted pyridines, furan, thiophene and derivatives, and N-Boc-indole (Boc=tert-butyloxycarbonyl). Of the electrophiles employed to attempt the interception of the generated aryl cuprates, aroyl chlorides, iodomethane, and diphenyl disulfide efficiently reacted. In addition, different oxidative agents were identified to afford symmetrical biaryls. Finally, palladium-catalyzed coupling with aryl halides was optimized and allowed the synthesis of different aryl derivatives in medium to good yields.
Efficient diphosphane-based catalyst for the palladium-catalyzed suzuki cross-coupling reaction of 3-pyridylboronic acids
Fu, Xing-Li,Wu, Lei-Lei,Fu, Hai-Yan,Chen, Hua,Li, Rui-Xiang
experimental part, p. 2051 - 2054 (2009/09/06)
A highly active catalyst system derived from PdCl2 and 2,2',6,6'- tetramethoxy-4,4'-bis(diphenylphosphanyl)-3,3'-bi- pyridine (P-Phos) has been developed for the Suzuki cross- coupling reaction of pyridylboronic acid with a variety of aryl halides in good to excellent yields, even in the presence of hindered and functional groups. In addition, P-Phos also exhibited high activity in the palladium-catalyzed Suzuki reaction of 2,6-dimethoxypyridylboronic acid in excellent yields with a fast rate. The steric and electronic effects of the P- Phos-palladium complex to this cross-coupling reaction were also discussed.
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).
