Oxidative cross-coupling of quinoxalinones with indoles enabled by acidochromism

An oxidative cross-coupling of quinoxalinones with indole derivatives via B(C 6 F 5 ) 3 ·H 2 O induced acidochromism of quinoxalinone derivatives was developed under mild and external photocatalyst-free conditions. The reaction shows excellent substrate scope, accommodating a wide range of functiona...

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Veröffentlicht in:Organic & biomolecular chemistry 2023-03, Vol.21 (13), p.279-2714
Hauptverfasser: Huang, Jie, Wang, Long, Tang, Xiang-Ying
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Sprache:eng
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Zusammenfassung:An oxidative cross-coupling of quinoxalinones with indole derivatives via B(C 6 F 5 ) 3 ·H 2 O induced acidochromism of quinoxalinone derivatives was developed under mild and external photocatalyst-free conditions. The reaction shows excellent substrate scope, accommodating a wide range of functional groups. The usefulness of this strategy was demonstrated by the synthesis of the natural products Azacephalandole A and Cephalandole A in high yields. Moreover, the products are fluorophores showing prevalent fluorescence properties with a wide emission range and good relative quantum yields. We report a new gate for changing photo inactive compounds into photocatalysts with easy operation, good tolerance of functional groups, and considerable yield. We demonstrate the synthesis of the natural products Azacephalandole A and Cephalandole A in high yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob00280b