Photochemical C−H Hydroxyalkylation of Quinolines and Isoquinolines

• Published in: Angewandte Chemie International Edition Vol. 58; no. 47; pp. 16878 - 16883
• Main Authors: Bieszczad, Bartosz, Perego, Luca Alessandro, Melchiorre, Paolo
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 18.11.2019; Wiley Subscription Services, Inc; John Wiley and Sons Inc
• Edition: International ed. in English
• Subjects: Chemistry; Chemistry, Multidisciplinary; Communication; Communications; dihydropyridines; Electromagnetic absorption; Functional groups; Minisci reaction; Natural products; Organic compounds; Oxidants; Oxidizing agents; Photochemicals; photochemistry; Physical Sciences; Quinolines; radical chemistry; Science & Technology; synthetic methods; HOMOLYTIC ACYLATION; ALKYLATION; ARYLATION; FUNCTIONALIZATION; NUCLEOPHILIC CHARACTER; HETEROARENES; HETEROCYCLES; photochemistry; dihydropyridines; SUBSTITUTIONS; Minisci reaction; RADICALS; radical chemistry; synthetic methods; ALKALOIDS

We report herein a visible light‐mediated C−H hydroxyalkylation of quinolines and isoquinolines that proceeds via a radical path. The process exploits the excited‐state reactivity of 4‐acyl‐1,4‐dihydropyridines, which can readily generate acyl radicals upon blue light absorption. By avoiding the nee...