893732-46-2Relevant academic research and scientific papers
A simple and efficient protocol for a palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF
Liu, Chun,Ni, Qijian,Bao, Fanying,Qiu, Jieshan
, p. 1260 - 1266 (2011)
A convenient, effective and mild protocol has been developed for the palladium-catalyzed ligand-free Suzuki reaction of aryl bromides with arylboronic acids in aqueous N,N-dimethylformamide (DMF) in the presence of K2CO3 and a catalytic amount of PdCl2 in air at room temperature. It is noteworthy that the volume ratio of water-DMF and base play important roles in the reaction, and various functional groups are tolerated under the optimized conditions. Furthermore, this protocol could be extended to the cross-couplings of nitrogen-based heteroaryl halides with arylboronic acids in moderate to excellent yields.
Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides
Markovic, Tim,Rocke, Benjamin N.,Blakemore, David C.,Mascitti, Vincent,Willis, Michael C.
, p. 4437 - 4442 (2017/07/11)
Pyridine rings are ubiquitous in drug molecules; however, the pre-eminent reaction used to form carbon-carbon bonds in the pharmaceutical industry, the Suzuki-Miyaura cross-coupling reaction, often fails when applied to these structures. This phenomenon is most pronounced in 2-substituted pyridines, and results from the difficulty in preparing, the poor stability of, and low efficiency in reactions of pyridine-2-boronates. We demonstrate that by replacing these boronates with pyridine-2-sulfinates, a cross-coupling process of unrivalled scope and utility is realized. The corresponding 3-And 4-substituted pyridine variants are also efficient coupling partners. In addition, we apply these sulfinates in a library format to the preparation of medicinally relevant derivatives of the drugs varenicline (Chantix) and mepyramine (Anthisan).
Oxygen-promoted Pd/C-catalyzed Suzuki-Miyaura reaction of potassium aryltrifluoroborates
Liu, Chun,Liu, Chao,Li, Xin-Min,Gao, Zhan-Ming,Jin, Zi-Lin
, p. 631 - 634 (2016/05/19)
A simple and highly efficient protocol has been developed for the Pd/C-catalyzed ligand-free Suzuki-Miyaura reaction of potassium aryltrifluoroborates. In this catalytic system, the results demonstrate that oxygen plays a positive role in the cross-coupling reaction. In addition, this catalytic system could be successfully applied to synthesize biaryl compounds containing a carbazole moiety and the catalyst was recycled seven times without significant loss of catalytic activity.
Thermoregulated ligand-palladium-catalyzed Suzuki reaction in water
Liu, Ning,Liu, Chun,Yan, Bo,Jin, Zilin
experimental part, p. 168 - 172 (2012/04/04)
An efficient and recyclable protocol for the Suzuki reaction in water has been developed based on the cloud point of thermoregulated ligand Ph 2P(CH2CH2O)nCH3 (n = 22). This method allows the preparation of a variety of biaryls in high yields and the catalytic system can be recycled four times with high efficiency.
A general and highly efficient method for the construction of aryl-substituted N-heteroarenes
Liu, Chun,Han, Na,Song, Xiaoxiao,Qiu, Jieshan
supporting information; experimental part, p. 5548 - 5551 (2011/02/19)
A general, simple and highly efficient method has been developed for the Pd(OAc)2-catalyzed ligand-free and aerobic Suzuki reaction of N-heteroaryl halides, which is strongly dependent on the molecular structure of solvent. A general, simple and highly efficient method has been developed for the Pd(OAc)2-catalyzed ligand-free and aerobic Suzuki reaction of N-heteroaryl halides including 2-pyridyl bromides, 3-pyridyl bromides, 3-quinolyl bromides, 5-pyrimidyl bromides and 2-pyrazyl chloride, which is strongly dependent on the molecular structure of solvent.
The 1,3-diaminobenzene-derived aminophosphine palladium pincer complex {C6H3[NHP(piperidinyl)2]2Pd(Cl)} - A highly active Suzuki-Miyaura catalyst with excellent functional group tolerance
Bolliger, Jeanne L.,Frech, Christian M.
experimental part, p. 1075 - 1080 (2010/06/17)
The rapidly prepared 1,3-diaminobenzenederived aminophosphine pincer complex {C6H3 [NHP(piperidinyl)2] 2Pd(Cl)} (1) is an effective Suzuki catalyst with excellent functional group tolerance. Side-product formations, such as homocoupling, debromation or protodeboration have only rarely been detected and if so, were in all cases below the 5% level. The presented reaction protocol is universally applicable. Experimental observations indicate that palladium nanoparticles are the catalytically active form of 1.
