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 - Článek v odborném periodiku
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
Grant CEP: GA ČR(CZ) GX20-03691X
Institucionální podpora: RVO:61388955
Klíčová slova: diels-alder reaction * enantioselective synthesis * in-vitro * cation * tetrahydroquinolines * inhibitors * cycloaddition * quinolines * aldimines * aldehydes
Obor OECD: Physical chemistry
Impakt faktor: 2.863, rok: 2020
Způsob publikování: Omezený přístup

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.
Trvalý link: http://hdl.handle.net/11104/0312783