61704-26-5Relevant articles and documents
Formate-Mediated Cross-Electrophile Reductive Coupling of Aryl Iodides and Bromopyridines
Schwartz, Leyah A.,Spielmann, Kim,Swyka, Robert A.,Xiang, Ming,Krische, Michael J.
, p. 298 - 301 (2020/10/19)
Two catalytic systems for the formate-mediated cross-electrophile reductive coupling of aryl iodides with 6-bromopyridines are described. Using homogenous rhodium or heterogeneous palladium catalysts, the products of reductive biaryl cross-coupling could
Borenium-Catalyzed Reduction of Pyridines through the Combined Action of Hydrogen and Hydrosilane
Clarke, Joshua J.,Maekawa, Yuuki,Nambo, Masakazu,Crudden, Cathleen M.
supporting information, p. 6617 - 6621 (2021/09/02)
Mesoionic carbene-stabilized borenium ions efficiently reduce substituted pyridines to piperidines in the presence of a hydrosilane and a hydrogen atmosphere. Control experiments and deuterium labeling studies demonstrate reversible hydrosilylation of the pyridine, enabling full reduction of the N-heterocycle under milder conditions. The silane is a critical reaction component to prevent adduct formation between the piperidine product and the borenium catalyst.
Palladium-Catalyzed Cascade Reactions of I-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines
Chen, Jiuxi,Hu, Maolin,Li, Renhao,Liu, Jichao,Qi, Linjun,Shao, Yinlin,Yao, Xinrong,Zhao, Zhiwei,Zhen, Qianqian
supporting information, p. 114 - 119 (2020/03/25)
This study presents the first example of the Pd-catalyzed cascade reactions of 5-oxohexanenitrile with arylboronic acids, affording important synthon 2-methylpyridines that can be further translated through C(sp3)-H functionalization to construct pyridine derivatives. Furthermore, this chemistry allows 5-oxo-5-Arylpentanenitrile to react with arylboronic acids to provide unsymmetrical 2,6-diarylpyridines. This protocol paves the way for the practical and atom economical syntheses of valuable pyridines with broad functional groups in moderate to excellent yields under mild conditions.
NNN-Ruthenium Catalysts for the Synthesis of Pyridines, Quinolines, and Pyrroles by Acceptorless Dehydrogenative Condensation
Deng, Danfeng,Hu, Bowen,Yang, Min,Chen, Dafa
, p. 2386 - 2394 (2018/07/31)
The bidentate ruthenium complex (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)2Cl2 (2) could transform to a tridentate product (HO-C5H3N-CO-C5H3N-C5H4N)Ru(CO)Cl2 (3), which further reacted with CH3ONa in the presence of PPh3 to convert to two complexes [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)2(CO)]Cl- (4) and [(OC5H3N-CO-C5H3N-C5H4N)Ru(PPh3)(CO)Cl] (5), via -OH deprotonation. The catalytic coupling cyclizations of secondary alcohols with amino alcohols were investigated, and complex 3 exhibited the highest activity. The coupling reactions proceeded in air with only 0.2 mol % catalyst loading and had a broad scope for the synthesis of pyridines, quinolones, and pyrroles.
A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents
Ramakrishna, Visannagari,Rani, Morla Jhansi,Reddy, Nareddula Dastagiri
, p. 7238 - 7255 (2018/01/01)
The Suzuki–Miyaura cross-coupling (SMC) reactions of several heteroaryl chlorides, benzyl chlorides, and aryl acid chlorides with (hetero)arylboron reagents have been investigated in the presence of [Pd(HL1)(PPh3)Cl2] (I) [HL1 = 3-[(2,6-diisopropylphenyl)-1-imidazolio]-2-quinoxalinide] as catalyst and K2CO3 as base in neat water. The synthesis of the heterocycle-containing biaryls required the addition of 2 mol-% of a phosphine ligand (PPh3 or X-Phos). A combination of more than 115 substrates were screened and it was found that I is a versatile catalyst that can produce heterocycle-containing biaryls, diarylmethanes, and benzophenones in moderate-to-excellent yields.
Direct C(sp3)-H Cross Coupling Enabled by Catalytic Generation of Chlorine Radicals
Shields, Benjamin J.,Doyle, Abigail G.
supporting information, p. 12719 - 12722 (2016/10/13)
Here we report the development of a C(sp3)-H cross-coupling platform enabled by the catalytic generation of chlorine radicals by nickel and photoredox catalysis. Aryl chlorides serve as both cross-coupling partners and the chlorine radical source for the α-oxy C(sp3)-H arylation of cyclic and acyclic ethers. Mechanistic studies suggest that photolysis of a Ni(III) aryl chloride intermediate, generated by photoredox-mediated single-electron oxidation, leads to elimination of a chlorine radical in what amounts to the sequential capture of two photons. Arylations of a benzylic C(sp3)-H bond of toluene and a completely unactivated C(sp3)-H bond of cyclohexane demonstrate the broad implications of this manifold for accomplishing numerous C(sp3)-H bond functionalizations under exceptionally mild conditions.
HETEROCYCLIC COMPOUND FOR ORGANIC ELECTROLUMINESCENCE ELEMENT AND APPLICATION OF THE SAME
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Paragraph 0327; 0328, (2016/10/09)
PROBLEM TO BE SOLVED: To provide a compound to be used for an electron transport material for an organic electroluminescence element excellent in a long service life. SOLUTION: A cyclic azine compound is provided, which has at least one substituent selected from the following groups having a substituent selected from alkyl, alkoxyl, halogen, amino, phosphyl, silyl, thiol, and acyl, on at least one of carbon atoms adjoining to a nitrogen atom. These groups are: azabenzene, diazabenzene, triazine, azanaphthalene, diazanaphthalene, triazanaphthalene, tetraazanaphthalene, pentaazanaphthalene, azaanthracene, diazaanthracene, triazaanthracene, tetraazaanthracene, pentaazaanthracene, hexaazaanthracene, heptaazaanthracene, azaphenanthrene, diazaphenanthrene, triazaphenanthrene, tetraazaphenanthrene, and the like. COPYRIGHT: (C)2015,JPOandINPIT
Kumada-corriu cross-couplings with 2-pyridyl grignard reagents
Ackermann, Lutz,Potukuchi, Harish K.,Kapdi, Anant R.,Schulzke, Carola
experimental part, p. 3300 - 3303 (2010/06/19)
Chemical Equation Presentation SPOs meet the challenge: A palladium complex derived from air- and moisture-stable secondary phosphine oxide (SPO) (1-Ad)2P(O)H enables general cross-coupling reactions of challenging electron-deficient 2-pyridyl Grignard reagents with ample scope (see scheme)
