Flavin-Catalyzed Aerobic α-Functionalization of 1,2,3,4-Tetrahydro-isoquinolines: Application to C=O and C–O Bond Formation
Abstract
Under metal- and light-free conditions, cationic flavin catalysts enable the aerobic α-functionalization of 1,2,3,4-tetrahydroisoquinolines: (i) α-oxygenation to 3,4-dihydroisoquinolones (C=O formation) and (ii) α-alkoxylation (C-O formation) via cross-dehydrogenative coupling with alcohols. The aerobic α-C=O and C-O bond formations occur via two complementary α-C-H activation pathways catalyzed by flavins with tunable redox properties. These reactions proceed in molecular oxygen or air atmospheres (1 atm) without any additional sacrificial reagents (e.g., external reductants) and without light, unlike conventional flavin-catalyzed aerobic oxidation reactions.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Oxidative Organic Chemistry Reactions
Radical Photochemical Reactions
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Volume
- 91
- Issue
- 3
- Pages
- 1355–1360
- Publication date
- 7 January 2026
- Language
- EN