Oxidative cross-coupling of quinoxalinones with indoles enabled by acidochromism
Jie Huang1, Long Wang1, Xiang-Ying Tang1
1Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Engineering Research Center for Biomaterials and Medical Protective Materials, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, Semiconductor Chemistry Center, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology (HUST), Wuhan 430074, People's Republic of China. xytang@hust.edu.cn.
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.
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