title: Synthesis of highly functionalized polycyclic quinoxaline derivatives using visible-light photoredox catalysis.
abstract: A mild and facile method for preparing highly functionalized pyrrolo[1,2-a]quinoxalines and other nitrogen-rich heterocycles, each containing a quinoxaline core or an analogue thereof, has been developed. The novel method features a visible-light-induced decarboxylative radical coupling of ortho-substituted arylisocyanides and radicals generated from phenyliodine(III) dicarboxylate reagents and exhibits excellent functional group compatibility. A wide range of quinoxaline heterocycles have been prepared. Finally, a telescoped preparation of these polycyclic compounds by integration of the in-line isocyanide formation and photochemical cyclization has been established in a three-step continuous-flow system.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139 (USA).
authors.forename: Zhi
authors.initials: Z
authors.lastname: He
authors.forename: Minwoo
authors.initials: M
authors.lastname: Bae
authors.forename: Jie
authors.initials: J
authors.lastname: Wu
authors.forename: Timothy F
authors.initials: TF
authors.lastname: Jamison
mesh_terms: D002384:Catalysis; D003486:Cyanides / Q000737:chemistry; D003500:Cyclization; D008027:Light; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry*; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D003486:Cyanides; D011083:Polycyclic Compounds; D011758:Pyrroles; D011810:Quinoxalines; C531444:pyrrolo(1,2-a)quinoxaline
keywords: flow chemistry; heterocycles; isocyanide; photochemistry; radicals