Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2‐Vinyl Anilines. Issue 15 (16th July 2021)

• Record Type: Journal Article
• Authors: Mäkelä, Mikko K.; Bulatov, Evgeny; Malinen, Kiia; Talvitie, Juulia; Nieger, Martin; Melchionna, Michele; Lenarda, Anna; Hu, Tao; Wirtanen, Tom; Helaja, Juho
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 15(2021)
• Page Start: 3775
• Page End: 3782
• Publication Date: 2021-07-16
• Subjects: Carbocatalysis -- Quinoline -- Oxidative Dehydrogenation -- Electrocyclization; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100711
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Oxidized active carbon (oAC) catalyses the formation of polysubstituted quinolines from o ‐vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal‐free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The mechanistic studies imply that both the acid and quinoidic groups in oAC are integral for the catalytic manifold. Abstract :