Synthesis of quinolines via Friedlander reaction catalyzed by CuBTC metal-organic-framework

0389820 - ÚFCH JH 2013 RIV GB eng J - Journal Article
Pérez-Mayoral, E. - Musilová, Zuzana - Gil, B. - Marszalek, B. - Položij, M. - Nachtigall, P. - Čejka, Jiří
Synthesis of quinolines via Friedlander reaction catalyzed by CuBTC metal-organic-framework.
Dalton Transactions. Roč. 41, č. 14 (2012), s. 4036-4044. ISSN 1477-9226. E-ISSN 1477-9234
Institutional research plan: CEZ:AV0Z40400503
Keywords : EFFICIENT HETEROGENEOUS CATALYST * AUGMENTED-WAVE METHOD * SOLID ACID CATALYSTS
Subject RIV: CF - Physical ; Theoretical Chemistry
Impact factor: 3.806, year: 2012

Friedlander condensation between 2-aminoaryl ketones and different carbonyl compounds, catalyzed by CuBTC was investigated by a combination of various experimental techniques and by density functional theory based modelling. CuBTC exhibiting hard Lewis acid character showed highly improved catalytic activity when compared with other molecular sieves showing high concentraion of Lewis acid sites, e.g. in BEA and (Al)SBA-15. Polysubstituted quinolines were synthesized via a Friedlander reaction catalyzed by CuBTC under the solvent-free conditions. High concentration of active sites in CuBTC together with the concerted effect of a pair of adjacent Cu2+ coordinatively unsaturated active sites are behind a very high quinoline yield reached within a short reaction time. Results reported here make CuBTC a promising catalyst for other Lewis acid-promoted condensations, including those leading to biologically active compounds with a particular relevance for the pharmaceutical industry. The mechanism of a catalyzed Friedlander reaction investigated computationally is also reported.
Permanent Link: http://hdl.handle.net/11104/0218769