4385-68-6Relevant articles and documents
Formation of 4-arylpyridines from pyridinium salts under the action of methylammonium sulfite
Gromov,Kurchavov
, p. 1606 - 1609 (2003)
Reactions of pyridinium salts or nonquaternized pyridine with 4-methylpyridinium salts in the presence of methylammonium sulfite in aqueous methylamine afford 4-phenylpyridhie in 29-57% yields. The probable mechanism of ring transformation in simplest pyr
Cobalt-catalyzed cross-coupling of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium reagents
Cui, Yan-Ying,Na, Jin-He,Guo, Meng-Meng,Huang, Jie-Ying,Chu, Xue-Qiang,Rao, Weidong,Shen, Zhi-Liang
supporting information, (2022/02/16)
Cobalt-catalyzed cross-couplings of nitrogen-containing heterocyclic phosphonium salts with arylmagnesium halides proceeded efficiently with the aid of cobalt(II) catalyst and copper(I) salt in tetrahydrofuran at ambient temperature, producing the desired
Phosphonium Salts as Pseudohalides: Regioselective Nickel-Catalyzed Cross-Coupling of Complex Pyridines and Diazines
Zhang, Xuan,McNally, Andrew
, p. 9833 - 9836 (2017/08/08)
Heterobiaryls are important pharmacophores that are challenging to prepare by traditional cross-coupling methods. An alternative approach is presented where pyridines and diazines are converted into heteroaryl phosphonium salts and coupled with aryl boronic acids. Nickel catalysts are unique for selective heteroaryl transfer, and the reaction has a broad substrate scope that includes complex pharmaceuticals. Phosphonium ions also display orthogonal reactivity in cross-couplings compared to halides, enabling chemoselective palladium- and nickel-catalyzed coupling sequences.
Palladium-catalyzed decarboxylative cross-coupling of 3-pyridyl and 4-pyridyl carboxylates with aryl bromides
Chennamaneni, Lohitha Rao,William, Anthony D.,Johannes, Charles W.
, p. 1293 - 1296 (2015/03/04)
Decarboxylative cross-coupling of 3-pyridyl and 4-pyridyl carboxylates with aryl bromides is reported. Using a bimetallic system of Cu2O and Pd(PPh3)4, the scope of the reaction is demonstrated by the synthesis of 27 pyridine-containing biaryls in moderate to good yields.
Palladium dichloride adduct of N,N-bis-(diphenylphosphanylmethyl)-2- aminopyridine: Synthesis, structure and catalytic performance in the decarboxylative cross-coupling of 4-picolinic acid with aryl bromide
He, Run-Tian,Wang, Jian-Feng,Wang, Hui-Fang,Ren, Zhi-Gang,Lang, Jian-Ping
, p. 9786 - 9794 (2014/06/23)
Reaction of PdCl2 with N,N-bis-(diphenylphosphanylmethyl)-2- aminopyridine (bdppmapy) afforded a mononuclear complex [(bdppmapy)PdCl 2] (1). Compound 1 was characterized by elemental analysis, IR, 1H, 13C and 31P NMR, electrospray ion mass spectra (ESI-MS) and X-ray single crystal crystallography. The Pd(ii) center in 1 is chelated by bdppmapy, showing a cis-square planar geometry. With the assistance of additive Cu2O, complex 1 exhibited good catalytic activity toward the decarboxylative cross-coupling reactions between 4-picolinic acid and aryl bromides. In the presence of only 2 mol% catalyst, a family of 4-aryl-pyridines could be isolated in up to 83% yield.
Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes
Chen, Wen-Ching,Hsu, Yu-Chen,Shih, Wei-Chun,Lee, Ching-Yu,Chuang, Wen-Han,Tsai, Yi-Fang,Chen, Peter Ping-Yu,Ong, Tiow-Gan
supporting information; experimental part, p. 6702 - 6704 (2012/07/14)
An amino-linked nitrogen heterocyclic carbene (amino-NHC), 1-tBu, has been shown to mediate carbon-carbon coupling through the direct C-H functionalization of benzene and pyridine in the absence of a metal catalyst. Using EPR, the first spectroscopic evidence corroborating the single electron transfer mechanism for the metal-free carbon-carbon coupling manifold, as reported by others, is introduced.
Gold(I)-catalyzed direct C-H arylation of pyrazine and pyridine with aryl bromides
Li, Ming,Hua, Ruimao
supporting information; experimental part, p. 1478 - 1481 (2009/06/08)
An efficient procedure for the direct C-H arylation of electron-poor aromatics such as pyrazine and pyridine with aryl bomides is described. In the presence of catalytic amount of Cy3PAuCl and with the use of t-BuOK as base, pyrazine undergoes the direct C-H arylation with aryl bromides at 100 °C, and the yields of the arylated products depend on the nature of aryl bromides. In the cases of electron-rich aryl bromides used, the arylated pyrazines can be obtained in good to high yields. For electron-poor aryl bromides, the addition of AgBF4 is the crucial point to accelerate the coupling reaction to give the arylated products in moderate yields. Pyridine also reacts with electron-rich aryl bromides catalyzed by Cy3PAuCl to give a mixture of arylated regioisomers in moderate yield. However, in order to realize the direct C-H arylation of pyridine with electron-poor aryl bromides, the addition of silver salt as additive and a milder reaction temperature (60 °C) are required.
Sodium 2-(2-pyridin-3-ylethylamino)ethyl sulfonate: an efficient ligand and base for palladium-catalyzed Suzuki reaction in aqueous media
Pawar, Shivaji S.,Uppalla, Lavkumar S.,Shingare, Murlidhar S.,Thore, Shivaji N.
scheme or table, p. 5858 - 5862 (2009/04/04)
PdCl2, N-donor ligand and base mediated Suzuki coupling reaction of aryl halides and arylboronic acid in water are described. The corresponding Suzuki products were obtained in good to excellent yields.
Self-assembly of oligomeric porphyrin rings
Haycock, Richard A.,Hunter, Christopher A.,James, David A.,Michelsen, Ulrike,Sutton, Liam R.
, p. 2435 - 2438 (2007/10/03)
(equation presented) A cobalt porphyrin equipped with two different but geometrically complementary pyridine ligands self-assembles to form an unusually stable complex with approximately 12 porphyrin monomers arranged in a macrocyclic array.
THE PYRIDYL CATION AS A REACTIVE INTERMEDIATE IN THE PHOTOREACTION OF IODOPYRIDINES WITH BENZENES
Ohkura, Kazue,Seki, Koh-ichi,Terashima, Masanao,Kanaoka, Yuichi
, p. 3433 - 3436 (2007/10/02)
The electrophilic behavior of the reactive entity in the photosubstitution of benzenes with 2-iodopyridine was found to be ascribable to the intermediary 2-pyridyl cation, rather than the electrophilic 2-pyridyl radical.
