16576-25-3Relevant articles and documents
A convenient and practical heterogeneous palladium-catalyzed carbonylative Suzuki coupling of aryl iodides with formic acid as carbon monoxide source
You, Shengyong,Yan, Chenyu,Zhang, Rongli,Cai, Mingzhong
, (2019)
A practical heterogeneous palladium-catalyzed carbonylative Suzuki coupling of aryl iodides with arylboronic acids under carbon monoxide gas-free conditions has been developed using a bidentate phosphino-functionalized magnetic nanoparticle-immobilized palladium(II) complex as catalyst. Formic acid was utilized as the carbon monoxide source with dicyclohexylcarbodiimide as the activator, and a wide variety of biaryl ketones were generated in moderate to high yields. The new heterogeneous palladium catalyst can be prepared via a simple procedure and can easily be separated from a reaction mixture by simply applying an external magnet and recycled up to 10 times without any loss of activity.
Minisci aroylation of N-heterocycles using choline persulfate in water under mild conditions
Hunjan, Mandeep Kaur,Laha, Joydev K.,Tinwala, Ummehani
, p. 22853 - 22859 (2021/12/24)
Metal persulfate mediated thermal oxidative organic transformations invariably require a higher temperature and frequently use an organic solvent. The objective of this work was to develop persulfate mediated oxidative transformations that can be performed nearly at room temperature using water as a solvent. This report describes modified Minisci aroylation of isoquinolines with arylglyoxylic acids using choline persulfate and its pre-composition (choline acetate and K2S2O8) in water at 40 °C. A few other nitrogen heterocycles were also utilized affording various aroylated products in good to excellent yields. Unlike metal persulfate that could produce metal salt byproducts, a key feature of the chemistry reported herein includes the use of environmentally benign choline persulfate containing biodegradable choline as a counter-cation, the Minisci reaction demonstrated at 40 °C in water as the only solvent, and unconventional activation of persulfate. This journal is
Copper(i)-catalyzed tandem synthesis of 2-acylquinolines from 2-ethynylanilines and glyoxals
Chu, Xiaoxiao,Jia, Jian,Liu, Gang,Liu, Xiguang,Wang, Guanghui,Yu, Mingwu,Zhao, Ximei
supporting information, p. 11811 - 11814 (2021/11/30)
An efficient one-step synthesis of 2-acylquinolines using a copper-catalyzed tandem reaction of 2-ethynylanilines with glyoxals in the presence of piperidine has been developed. This new protocol successfully avoids multi-step operation and the use of highly toxic cyanides required in traditional methods, and provides a practical tool for synthetic and pharmaceutical chemists. Various 2-acylquinolines are obtained with perfect regioselectivity in moderate to good yields (up to 86%). The potential synthetic utility of this method is exemplified by a large-scale experiment and synthetic transformation of the products.
Synthesis method of 2-aroyl quinoline derivative
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Paragraph 0011, (2021/11/19)
The invention relates to a synthesis method of a 2-aroyl quinoline derivative, which comprises the following steps: by taking 2-bromoaniline and aryl cyclobutanol as reaction substrates, palladium chloride as a catalyst, tricyclohexylphosphine as a ligand, cesium carbonate as alkali and ultra-dry toluene as a solvent, stirring and reacting for 12 hours under the protection of nitrogen at 110 DEG C, then taking tetrabutylammonium iodide as a phase transfer catalyst, under the conditions of acetic acid and potassium persulfate, stirring and reacting for 16 hours at 90 DEG C by taking methylbenzene as a solvent; the method has the advantages of relatively low requirements on reaction conditions, mild conditions, simple operation steps, simple and easily available raw materials, great reduction of environmental pollution and the like.
Photo-redox catalyzed dehydrazinative acylation of N-heterocycles: Via Minisci reaction
Hafeez, Saira,Saeed, Aamer
, p. 38683 - 38689 (2021/12/20)
Visible light-induced acylation of heteroaromatic compounds have been achieved using benzoyl hydrazides as an efficient acyl source under mild reaction conditions. The photo-redox catalyzed oxidative cleavage of hydrazides leads to in situ formation of ac
Preparation method of 2-quinolylphenyl ketone compound
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Paragraph 0031-0035, (2021/11/10)
The invention discloses a preparation method of a 2-quinolylphenyl ketone compound. According to the preparation method, 2-acetenyl aniline, phenyl glyoxal and piperidine are used as initial raw materials, and are subjected to a gold-catalyzed three-component coupling reaction (A3 couplings) and an intramolecular condensation reaction so as to synthesize the 2-quinolylphenyl ketone in one step. The preparation method has the advantages of cheap and easily available raw materials, simple operation steps, mild reaction conditions, high atom economy and excellent regioselectivity, and meets the needs of large-scale industrial production. The prepared 2-quinolylphenyl ketone is an important active drug molecule and can be used as a cannabinoid CB2 receptor stimulant.
K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water
Hunjan, Mandeep Kaur,Laha, Joydev K.
, p. 8437 - 8440 (2021/09/02)
While persulfate activation at room temperature using glucose has primarily been focused on kinetic studies of the sulfate radical anion, the utilization of this protocol in organic synthesis is rarely demonstrated. We reinvestigated selected K2S2O8-mediated known organic reactions that invariably require higher temperatures and an organic solvent. A diverse, mild functionalization and synthesis of heterocycles using the inexpensive oxidant K2S2O8 in water at room temperature is reported, demonstrating the sustainability and broad scope of the method. Unlike traditional methods used for persulfate activation, the current method uses naturally abundant glucose as a K2S2O8 activator, avoiding the use of higher temperature, UV light, transition metals or bases.
From Pyridine- N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy
Bugaenko, Dmitry I.,Yurovskaya, Marina A.,Karchava, Alexander V.
supporting information, p. 6099 - 6104 (2021/08/03)
The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable organometallic reagents. The protocol operates at ambient temperature and tolerates sensitive functional groups, enabling the synthesis of otherwise challenging compounds.
Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using ‘Ene’-Reductases with Photoredox Catalysts
Biegasiewicz, Kyle F.,Black, Michael J.,Chung, Megan M.,Hyster, Todd K.,Meichan, Andrew J.,Nakano, Yuji,Sandoval, Braddock A.,Zhu, Tianyu
supporting information, p. 10484 - 10488 (2020/04/29)
Flavin-dependent ‘ene’-reductases (EREDs) are highly selective catalysts for the asymmetric reduction of activated alkenes. This function is, however, limited to enones, enoates, and nitroalkenes using the native hydride transfer mechanism. Here we demonstrate that EREDs can reduce vinyl pyridines when irradiated with visible light in the presence of a photoredox catalyst. Experimental evidence suggests the reaction proceeds via a radical mechanism where the vinyl pyridine is reduced to the corresponding neutral benzylic radical in solution. DFT calculations reveal this radical to be “dynamically stable”, suggesting it is sufficiently long-lived to diffuse into the enzyme active site for stereoselective hydrogen atom transfer. This reduction mechanism is distinct from the native one, highlighting the opportunity to expand the synthetic capabilities of existing enzyme platforms by exploiting new mechanistic models.
Rhodium-Catalyzed Pyridine N-Oxide Assisted Suzuki-Miyaura Coupling Reaction via C(O)-C Bond Activation
Zhong, Jing,Long, Yang,Yan, Xufei,He, Shiyu,Ye, Runyou,Xiang, Haifeng,Zhou, Xiangge
supporting information, p. 9790 - 9794 (2019/12/24)
A rhodium-catalyzed Suzuki-Miyaura coupling reaction via C(O)-C bond activation to form 2-benzoylpyridine N-oxide derivatives is reported. Both the C(O)-C(sp2) and C(O)-C(sp3) bond could be activated during the reaction with yields up to 92%. The N-oxide moiety could be employed as a traceless directing group, leading to free pyridine ketones.
