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Iodinated (Perfluoro)alkyl Quinoxalines by Atom Transfer Radical Addition Using ortho ‐Diisocyanoarenes as Radical Acceptors
Author(s) -
Leifert Dirk,
Studer Armido
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201606023
Subject(s) - quinoxaline , chemistry , alkyl , azobisisobutyronitrile , alkylation , atom transfer radical polymerization , combinatorial chemistry , medicinal chemistry , photochemistry , organic chemistry , catalysis , polymer , copolymer , polymerization
A simple method for the preparation of functionalized quinoxalines is reported. Starting from readily accessible ortho ‐diisocyanoarenes and (perfluoro)alkyl iodides, the quinoxaline core is constructed during (perfluoro)alkylation by atom transfer radical addition (ATRA), resulting in 2‐iodo‐3‐(perfluoro)alkylquinoxalines. The radical cascades are readily initiated either with visible light or by using α,α′‐azobisisobutyronitrile (AIBN). The heteroarene products are obtained in high yields (up to 94 %), and the method can be readily scaled up. Useful follow‐up chemistry documents the value of the novel radical quinoxaline synthesis.