Six N-alkyl-4'-methyl-1,1'-biphenyl-2-sulfonamides were synthesized facilely and efficiently from low cost and readily available benzenesulfonyl chloride and C1-C4 fatty amines via linking DoM reaction with Suzuki r...Six N-alkyl-4'-methyl-1,1'-biphenyl-2-sulfonamides were synthesized facilely and efficiently from low cost and readily available benzenesulfonyl chloride and C1-C4 fatty amines via linking DoM reaction with Suzuki reaction.The structures of the new compounds synthesized were confirmed by elemental analysis,IR,1H NMR and MS.This new method makes a feature of low cost and readily available starting material,fewer steps,mild condition,easiness to operate and higher yield.展开更多
Highly active, air-stable and water-soluble palladium-phosphinous acid complexes have been applied to Suzuki cross-coupling reaction of heteroaryl bromides under mild conditions in water/alcoholic solvents. Suzuki cro...Highly active, air-stable and water-soluble palladium-phosphinous acid complexes have been applied to Suzuki cross-coupling reaction of heteroaryl bromides under mild conditions in water/alcoholic solvents. Suzuki cross-coupling reaction of heteroaryl bromides with phenylboronic acid occurred efficiently using palladium phosphinous acid complexes (POPd) and phase transfer catalyst (tetrabutylammonium bromide and polyethylene glycol) in water/ethanol mixture, water/propanol mixture and neat water respectively, the corresponding yields of cross-coupling heteroaryl-aryls were satisfied. The tert-butyl substituted ligand di-tert-butylphosphino in combination with POPd was found to be more active than the same family derived catalysts dipalladium complexes POPdl and POPd2, and other two kinds of Pd-catalysts Pd(PPh3)4 and Pd2(dba)3. The mechanism of Suzuki cross-coupling reaction between heteroaryl bromides and phenylboronic acid in water was proposed with respect to the key role of phase transfer catalyst on the transmetallation step. Compared with other solid phase transfer catalysts, TBAB was tested as the ideal one. The alkalinity of base and the molar proportion between POPd and TBAB were investigated in water and alcoholic solvents. Notably, in the presence of TBAB adding alcoholic solvents into water enhanced the yields of target products. However in terms of the liquid phase transfer catalyst of PEGs, mixing water into PEGs could slightly decrease the yields with respect to the water free PEGs bulk phase, which was probably due to the homogenous liquid conditions in pure PEGs and weak interactions between PEGs and heteroaryl bromide molecules in water depending on their molecular chain lengths.展开更多
A palladium catalyst supported on 2-amino- pyridine functionalized cellulose was synthesized and fully characterized by inductively coupled plasma atomic emission spectroscopy, transmission electron microscope, Fourie...A palladium catalyst supported on 2-amino- pyridine functionalized cellulose was synthesized and fully characterized by inductively coupled plasma atomic emission spectroscopy, transmission electron microscope, Fourier transform infrared spectroscopy, thermogravi- metric analysis and X-ray photoelectron spectrometry. This catalyst can be applied in the Suzuki cross-coupling reaction of aryl halides with arylboronic acids in 50% ethanol to afford biaryls in good yields, and easily recycled by simple filtration after reaction without the loss of metal Pd.展开更多
Pyrazoles and their derivatives are important heterocycles found in nature and present in numerous bioactive compounds.In contrast to 3 or 5-aryl pyrazole,the preparation of 4-aryl pyrazole is fairly rare.Utilizing mi...Pyrazoles and their derivatives are important heterocycles found in nature and present in numerous bioactive compounds.In contrast to 3 or 5-aryl pyrazole,the preparation of 4-aryl pyrazole is fairly rare.Utilizing microwave irradiation,the synthesis of 4-substituted-arylpyrazole via Suzuki cross-coupling has been developed with a wide range of substrates.The remarkable advantages of this method are mild reaction conditions,simple operation,high yield,and short reaction time.Product structures were identified by MS 1H NMR 13C NMR,and elemental analysis.展开更多
文摘Six N-alkyl-4'-methyl-1,1'-biphenyl-2-sulfonamides were synthesized facilely and efficiently from low cost and readily available benzenesulfonyl chloride and C1-C4 fatty amines via linking DoM reaction with Suzuki reaction.The structures of the new compounds synthesized were confirmed by elemental analysis,IR,1H NMR and MS.This new method makes a feature of low cost and readily available starting material,fewer steps,mild condition,easiness to operate and higher yield.
基金supported by the Natural Science Foundation of Liaoning Education Department (No. 2008T094)
文摘Highly active, air-stable and water-soluble palladium-phosphinous acid complexes have been applied to Suzuki cross-coupling reaction of heteroaryl bromides under mild conditions in water/alcoholic solvents. Suzuki cross-coupling reaction of heteroaryl bromides with phenylboronic acid occurred efficiently using palladium phosphinous acid complexes (POPd) and phase transfer catalyst (tetrabutylammonium bromide and polyethylene glycol) in water/ethanol mixture, water/propanol mixture and neat water respectively, the corresponding yields of cross-coupling heteroaryl-aryls were satisfied. The tert-butyl substituted ligand di-tert-butylphosphino in combination with POPd was found to be more active than the same family derived catalysts dipalladium complexes POPdl and POPd2, and other two kinds of Pd-catalysts Pd(PPh3)4 and Pd2(dba)3. The mechanism of Suzuki cross-coupling reaction between heteroaryl bromides and phenylboronic acid in water was proposed with respect to the key role of phase transfer catalyst on the transmetallation step. Compared with other solid phase transfer catalysts, TBAB was tested as the ideal one. The alkalinity of base and the molar proportion between POPd and TBAB were investigated in water and alcoholic solvents. Notably, in the presence of TBAB adding alcoholic solvents into water enhanced the yields of target products. However in terms of the liquid phase transfer catalyst of PEGs, mixing water into PEGs could slightly decrease the yields with respect to the water free PEGs bulk phase, which was probably due to the homogenous liquid conditions in pure PEGs and weak interactions between PEGs and heteroaryl bromide molecules in water depending on their molecular chain lengths.
基金Acknowledgements This work was supported by National Natural Science Foundation of China (Grant No. 20972109) and National Youth Science Foundation of China (No. 51403151).
文摘A palladium catalyst supported on 2-amino- pyridine functionalized cellulose was synthesized and fully characterized by inductively coupled plasma atomic emission spectroscopy, transmission electron microscope, Fourier transform infrared spectroscopy, thermogravi- metric analysis and X-ray photoelectron spectrometry. This catalyst can be applied in the Suzuki cross-coupling reaction of aryl halides with arylboronic acids in 50% ethanol to afford biaryls in good yields, and easily recycled by simple filtration after reaction without the loss of metal Pd.
基金the National Nature Science Foundation of China (Nos. 21002038 and 21272091) for the financial support
文摘Pyrazoles and their derivatives are important heterocycles found in nature and present in numerous bioactive compounds.In contrast to 3 or 5-aryl pyrazole,the preparation of 4-aryl pyrazole is fairly rare.Utilizing microwave irradiation,the synthesis of 4-substituted-arylpyrazole via Suzuki cross-coupling has been developed with a wide range of substrates.The remarkable advantages of this method are mild reaction conditions,simple operation,high yield,and short reaction time.Product structures were identified by MS 1H NMR 13C NMR,and elemental analysis.