36680-26-9Relevant academic research and scientific papers
Ru(II)–NNO pincer-type complexes catalysed E-olefination of alkyl-substituted quinolines/pyrazines utilizing primary alcohols
Balamurugan, Gunasekaran,Malecki, Jan Grzegorz,Ramesh, Rengan,Tamilthendral, Veerappan
, (2022/01/08)
An efficient and selective E-olefination of alkyl-substituted quinolines and pyrazines through acceptorless dehydrogenative coupling of alcohols catalysed by Ru(II)–N^N^O pincer-type complexes encompassing carbonyl and triphenylarsines as co-ligands is de
Deaminative Olefination of Methyl N-Heteroarenes by an Amine Oxidase Inspired Catalyst
Thorve, Pradip Ramdas,Maji, Biplab
supporting information, p. 542 - 547 (2021/01/26)
We explored the bioinspired o-quinone cofactor catalyzed aerobic primary amine dehydrogenation for a cascade olefination reaction with nine different methyl N-heteroarenes, including pyrimidines, pyrazines, pyridines, quinolines, quinoxolines, benzimidazoles, benzoxazoles, benzthiazoles, and triazines. An o-quinone catalyst phd (1,10-phenanthroline-5,6-dione) combined with a Br?nsted acid catalyzed the reaction. N-Heteroaryl stilbenoids were synthesized in high yields and (E)-selectivities under mild conditions using oxygen (1 atm) as the sole oxidant without needing transition-metal salt, ligand, stoichiometric base, or oxidant.
Preparation method of alkyl/alkenyl substituted nitrogen-containing heterocyclic compound
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Paragraph 0066-0074, (2021/07/10)
The invention belongs to the technical field of organic synthesis, and particularly discloses a preparation method of an alkyl/alkenyl substituted nitrogen-containing heterocyclic compound, which comprises the following steps: (1) adding a 2-methyl nitrogen-containing heterocyclic compound, primary alcohol, alkali and an additive into an organic solvent, performing stirring reaction for 24 hours, and then cooling the product to room temperature; and (2) concentrating, separating and purifying the reaction liquid obtained in the step (1). The simple and effective method for preparing the alkyl/alkenyl substituted nitrogen-containing heterocyclic compound under the metal-free and ligand-free conditions is realized, the 2-methyl nitrogen-containing heterocyclic compound and the primary alcohol which are economical and easy to obtain are used as raw materials, and the alkyl/alkenyl substituted nitrogen-containing heterocyclic compound is prepared under the synergistic promotion of alkali and additives; and methyl alkylation and alkenylation reaction are carried out to generate the corresponding alkyl/alkenyl substituted nitrogen-containing heterocyclic compound. The product has high application value and can be used in the fields of spices, medicines, materials, organic synthesis and the like. The method is wide in application range, simple in process, green, simple, high in yield and suitable for popularization and application.
Metal-Free Synthesis of Alkenylazaarenes and 2-Aminoquinolines through Base-Mediated Aerobic Oxidative Dehydrogenation of Benzyl Alcohols
Batra, Sanjay,Dahatonde, Dipak J.,Ghosh, Aritra
, p. 2746 - 2751 (2021/06/25)
A metal-free, base-mediated, and atom-efficient oxidative dehydrogenative coupling of substituted phenylmethanols (benzyl alcohols) with methyl azaarenes or phenylacetonitriles to afford substituted alkenylazaarenes or 2-aminoquinolines, respectively is described. CsOH.H2O was discovered to be the base of choice for obtaining optimal yields of the title compounds, although the reaction could proceed with KOH as well. The protocol that works efficiently in the presence of air is amenable over broad range of substrates.
Method for alkenylation of methyl heterocyclic compound
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Paragraph 0115-0118, (2021/02/10)
The invention discloses a method for alkenylation of methyl heterocyclic compound, which is a green method for synthesizing an alkenyl heterocyclic compound by carrying out alkenylation reaction on methyl under the condition that the methyl heterocyclic compound and alcohol do not need to participate in a transition metal catalyst. According to the method, alcohol which is cheap, easy to obtain, wide in source, stable and low in toxicity is used as an alkenylation reagent, no transition metal catalyst or ligand is needed, air can be directly used as a convenient, mild and efficient oxidizing agent under the action of common water-soluble inorganic base, and the method is suitable for industrial production. The alkenyl heterocyclic compound is directly synthesized by carrying out a Cenylation reaction with a methyl heterocyclic compound through processes such as oxidative condensation and the like. The method has the advantages of simple reaction conditions, no need of inert gas protection, low requirements on equipment, easiness in operation, water as a byproduct, easiness in removal of water-soluble inorganic base, no metal residue in the product, easiness in purification, suitability for heterocyclic systems such as quinoline, quinoxaline, pyridine, benzothiazole and the like, and wide application range, thereby having certain research significance and potential application prospect.
Role of Benzylic Deprotonation in Nickel-Catalyzed Benzylic Dehydrogenation
Zhang, Pengpeng,Cantrell, Rachel L.,Newhouse, Timothy R.
supporting information, p. 1652 - 1656 (2021/07/31)
Alkylarenes are readily functionalized via the corresponding benzylic anions. Benzylic anions have been used for a range of catalytic reactions, including Ni-catalyzed dehydrogenation. Interestingly, the employment of Zn(TMP) 2for slow and incomplete deprotonation of the benzylic position was observed. This manuscript describes a preliminary investigation into the deprotonation of heteroarenes and its relationship to Ni-catalyzed benzylic dehydrogenation.
Aryl-Nickel-Catalyzed Benzylic Dehydrogenation of Electron-Deficient Heteroarenes
Zhang, Pengpeng,Huang, David,Newhouse, Timothy R.
supporting information, p. 1757 - 1762 (2020/02/04)
This manuscript describes the first practical benzylic dehydrogenation of electron-deficient heteroarenes, including pyridines, pyrazines, pyrimidines, pyridazines, and triazines. This transformation allows for the efficient benzylic oxidation of heteroarenes to afford heterocyclic styrenes by the action of nickel catalysis paired with an unconventional bromothiophene oxidant.
MnO2 mediated sequential oxidation/olefination of alkyl-substituted heteroarenes with alcohols
Zhang, Chunyan,Li, Zehua,Fang, Yanchen,Jiang, Shaohua,Wang, Maorong,Zhang, Guoying
supporting information, (2020/02/15)
A practical and efficient ligand-free MnO2 mediated sequential oxidation and olefination has been developed for the facile synthesis of a broad range of unsaturated N-heteroazaarenes from simple alkyl-substituted heteroarenes and alcohols. The procedure tolerates a series of functional groups, such as methoxyl, chloro, bromo, iodo, vinyl, phenolic and hetero groups, providing the olefination products in moderate to good yields.The protocol could be conducted at mild conditions and used environmentally friendly air as the clear oxidant.
Iron/TEMPO-catalyzed direct aerobic oxidative coupling of methyl-mubstituted N-heteroazaarenes with alcohols
Zhang, Zhiguang,Ma, Yantao,Dai, Siwei,Li, Ling,Zhang, Yong,Li, Hao
supporting information, (2020/04/21)
A novel direct oxidative coupling of methyl-substituted N-heteroazaarenes with alcohols has been developed to construct olefins under mild condition. The reaction is catalyzed by Fe(NO3)3·9H2O/TEMPO with oxygen as terminal oxidant. A variety of E-disubstituted olefins bearing diverse functional groups could be obtained selectively in moderate to excellent yields. The reaction is environmentally friendly and ligand-free.
Preparation method of trans-disubstituted olefin
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Paragraph 0038-0045, (2020/02/27)
The invention relates to the technical field of organic chemical synthesis, and in particular, relates to a preparation method of trans-disubstituted olefin. According to the preparation method, primary alcohol and methyl azacycle are taken as raw materials, transition metal salt, nitric oxide and alkali are taken as catalysts, an organic solution is taken as a reaction medium, and reaction is carried out in an oxygen atmosphere. According to the preparation method, a reaction by-product is only water, the environment is not polluted, the required transition metal catalyst is cheap and easy toobtain, the reaction does not need high temperature, and the reaction cost and the requirements on reaction conditions can be reduced.
