Oxidative cross-coupling of quinoxalinones with indoles enabled by acidochromism?

Organic & Biomolecular Chemistry Pub Date: 2023-03-02 DOI: 10.1039/D3OB00280B

Abstract

An oxidative cross-coupling of quinoxalinones with indole derivatives via B(C6F5)3·H2O 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.

Graphical abstract: Oxidative cross-coupling of quinoxalinones with indoles enabled by acidochromism
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