Helquats as Promoters of the Povarov Reaction: Synthesis of 1,2,3,4-Tetrahydroquinoline Scaffolds Catalyzed by Helicene-Viologen Hybrids

0534610 - ÚFCH JH 2021 RIV DE eng J - Journal Article
Reyes-Gutierrez, P. E. - Amatov, T. T. - Švec, P. - Císařová, I. - Šaman, D. - Pohl, R. - Teplý, F. - Pospíšil, Lubomír
Helquats as Promoters of the Povarov Reaction: Synthesis of 1,2,3,4-Tetrahydroquinoline Scaffolds Catalyzed by Helicene-Viologen Hybrids.
ChemPlusChem. Roč. 85, č. 10 (2020), s. 2212-2218. ISSN 2192-6506. E-ISSN 2192-6506
R&D Projects: GA ČR(CZ) GX20-03691X
Institutional support: RVO:61388955
Keywords : diels-alder reaction * enantioselective synthesis * in-vitro * cation * tetrahydroquinolines * inhibitors * cycloaddition * quinolines * aldimines * aldehydes
OECD category: Physical chemistry
Impact factor: 2.863, year: 2020
Method of publishing: Limited access

Helquats (HQs) are structurally linked to helicenes and viologens, and they represent an attractive field of research in chemistry and medicinal chemistry. In the present work they were used as catalysts for the synthesis of 1,2,3,4-tetrahydroquinolines in good yields by the Povarov reaction. The substrate scope and the capability of different helquats to promote Povarov reactions are demonstrated. Studies to elucidate mechanistic details revealed that helquats act as single-electron transfer oxidants through a cation-radical mechanism. The screening of the catalytic activity of HQs confirmed that an active HQ must have a LUMO energy below8.67 eV and the standard redox potential higher (less negative) than1.2 V vs. the ferrocene/ferrocenium redox couple.
Permanent Link: http://hdl.handle.net/11104/0312783