Iron-Catalyzed Oxidative Cyclization of 2‑Amino Styrenes with Alcohols and Methyl Arenes for the Synthesis of Polysubstituted Quinolines
Herein, we present the iron-catalyzed oxidative cyclization of alcohol/methyl arene with 2-amino styrene to synthesize polysubstituted quinoline. Low-oxidation level substrates such as alcohols and methyl arenes are converted to aldehydes in the presence of an iron catalyst and di-t-butyl peroxide....
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Veröffentlicht in: | Journal of organic chemistry 2023-07, Vol.88 (13), p.8099-8113 |
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Hauptverfasser: | , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Herein, we present the iron-catalyzed oxidative cyclization of alcohol/methyl arene with 2-amino styrene to synthesize polysubstituted quinoline. Low-oxidation level substrates such as alcohols and methyl arenes are converted to aldehydes in the presence of an iron catalyst and di-t-butyl peroxide. Then, the quinoline scaffold is synthesized through imine condensation/radical cyclization/oxidative aromatization. Our protocol showed a broad substrate scope, and various functionalization and fluorescence applications of quinoline products demonstrated its synthetic ability. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.3c00095 |