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Synthesis of Highly Functionalized Polycyclic Quinoxaline Derivatives Using Visible‐Light Photoredox Catalysis
Author(s) -
He Zhi,
Bae Minwoo,
Wu Jie,
Jamison Timothy F.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201408522
Subject(s) - quinoxaline , photoredox catalysis , chemistry , reagent , radical , visible spectrum , combinatorial chemistry , catalysis , photochemistry , isocyanide , photocatalysis , organic chemistry , materials science , optoelectronics
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.