1289213-22-4Relevant articles and documents
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
, (2020)
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.
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
NaCl as Catalyst and Water as Solvent: Highly E-Selective Olefination of Methyl Substituted N-Heteroarenes with Benzyl Amines and Alcohols
Hazra, Susanta,Tiwari, Vikas,Verma, Ashutosh,Dolui, Pritam,Elias, Anil J.
supporting information, p. 5496 - 5501 (2020/07/14)
Oxidative coupling of benzylamines and alcohols with methyl substituted N-heteroarenes such as quinolines and quinoxalines has been achieved using chloride, a sea abundant anion as the catalyst for practical synthesis of a wide range of E-disubstituted olefins in aqueous medium. Detailed mechanistic studies and control experiments were carried out to deduce the reaction mechanism which indicated that in situ formed ClO2- is the active form of the catalyst. We have successfully carried out a 1 g scale reaction using this methodology, and five pharmaceutically relevant conjugated olefins were also synthesized by this method in moderate to good yields.
Nickel-Catalyzed Direct Alkenylation of Methyl Heteroarenes with Primary Alcohols
Baidya, Mahiuddin,Ramakrishna, Isai,Ramalingam, Bose Muthu
, p. 9819 - 9825 (2019/08/26)
An efficient nickel-catalyzed acceptorless dehydrogenative coupling of methyl-substituted heteroarenes with primary alcohols is achieved using an in situ generated complex of inexpensive NiBr2 and readily available 8-aminoquinoline picolinic amide ligand. The protocol is operationally simple and scalable and furnishes a series of high-value 2-alkenylheteroarenes in good yields (up to 88percent) with exclusive E-selectivity. The reaction proceeds with the release of water and molecular hydrogen, which was analyzed through gas chromatography to validate the reaction mechanism. ?
Synthesis of (E)-2-Alkenylazaarenes via Dehydrogenative Coupling of (Hetero)aryl-fused 2-Alkylcyclic Amines and Aldehydes with a Cobalt Nanocatalyst
Zhou, Changjian,Tan, Zhenda,Jiang, Huanfeng,Zhang, Min
, p. 2887 - 2892 (2018/05/03)
To date, the synthesis of (E)-2-alkenylazaarenes via the condensation of 2-methyl N-heteroarenes with aldehydes or their equivalents has been well demonstrated. However, the direct formation of such a class of useful compounds from extensively distributed 2-alkylcyclic amine motifs remains an unresolved goal. Herein, by employing the nitrogen-silica-doped carbon (Vulcan XC-72R) as the support, we have developed a low-loading cobalt nanocatalyst (Co/N-Si-C). The combination of such a catalyst with p-nitrobenzoic acid and molecular O2 exhibits excellent catalytic performance towards the dehydrogenative coupling of (hetero)aryl-fused 2-alkylcyclic amines with aldehydes to afford the (E)-2-alkenylazaarenes. In the reaction, effective capture of the partially dehydrogenated cyclic amine motifs appears to be the key strategy to address the issue of the chemoselectivity. The developed catalytic transformation proceeds with the merits of broad substrate scope, good functional group tolerance, high atom-efficiency, use of an earth-abundant and reusable cobalt catalyst and molecular O2 as a green oxidant, which offers an important basis for the direct conversion of inert cyclic amine units into the functional frameworks.
Regiospecific C-N photocyclization of 2-styrylquinolines
Gulakova, Elena N.,Berdnikova, Daria V.,Aliyeu, Tseimur M.,Fedorov, Yuri V.,Godovikov, Ivan A.,Fedorova, Olga A.
, p. 5533 - 5537 (2014/07/08)
Regiospecific C-N photocyclization of 2-styrylquinolines resulting in formation of potentially biologically active quino[1,2-a]quinolizinium derivatives was investigated. The presence of strong electron-donating groups in the phenyl ring reveals to be a crucial factor managing photocyclization effectiveness. Introduction of a crown ether moiety allows changing the photoreaction parameters by means of complexation with Mg(ClO4) 2.
Oxidative olefination of secondary amines with carbon nucleophiles
Zhang, Yong-Gang,Xu, Jing-Kun,Li, Xi-Ming,Tian, Shi-Kai
supporting information, p. 3648 - 3652 (2013/07/19)
An unprecedented olefination reaction of secondary amines with carbon nucleophiles has been developed through C-N/C-H functionalization under metal-free oxidative conditions. In the presence of a stoichiometric amount of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), a range of secondary N-alkylanilines smoothly underwent oxidative olefination with 2-alkylazaarenes, acetophenone, and malononitrile to give structurally diverse polysubstituted alkenes in moderate to excellent yields with excellent (E) selectivity. Preliminary mechanistic studies revealed that the oxidative olefination reaction proceeds through amine oxidation followed by imine olefination. A range of secondary N-alkylanilines smoothly underwent DDQ-promoted oxidative olefination with 2-alkylazaarenes, acetophenone, and malononitrile to give structurally diverse alkenes in moderate to excellent yields with excellent (E) selectivity. Mechanistically, the reaction proceeds through amine oxidation followed by imine olefination (DDQ = 2,3-dichloro-5,6-dicyano-1,4-benzoquinone). Copyright
