38101-91-6Relevant articles and documents
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.
Waste-minimized synthesis of C2 functionalized quinolines exploiting iron-catalysed C-H activation
Ferlin, Francesco,Zangarelli, Agnese,Lilli, Simone,Santoro, Stefano,Vaccaro, Luigi
, p. 490 - 495 (2021/01/28)
Herein we present an efficient and regioselective iron-catalyzed methodology for the external oxidant-free functionalization of quinoline-N-oxides. The protocol, based on the use of inexpensive and easily accessible FeSO4, showed broad applicability to a wide range of substrates. An additional green feature of this synthetic methodology is H2O being the only by-product. Experimental and computational investigations provide support to a mechanism based on a facile C-H activation event. The green efficiency of the process has also been carefully assessed using: (i) metrics related to the synthetic process (AE, Yield, 1/SF, MRP and RME); (ii) safety/hazard metrics (SHZI and SHI); and (iii) metrics related to the metal used as the catalyst (Abundance, OEL and ADP). In addition to the many advantages of this protocol related to the green iron catalyst used and the safety/hazard features of the process, an E-factor value of ca. 0.92 (84 to >99% reduction compared to known protocols) evidently confirms the sustainable efficiency of the procedure presented. Practical utility has also been demonstrated by performing the reaction efficiently on a multi-gram scale. This journal is