Copper-Catalyzed Aerobic Oxidative Dicarbonylation of Indoles toward Solvatochromic Fluorescent Indole-Substituted Quinoxalines

被引:26
作者
Zhang, Zeguang [1 ]
Dai, Zhihong [1 ]
Jiang, Xuefeng [1 ,2 ]
机构
[1] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
关键词
alpha-hydroxyketones; dicarbonylation; indoles; quinoxalines; solvatochromism; C BOND-CLEAVAGE; INTRAMOLECULAR CHARGE-TRANSFER; DIOXYGEN ACTIVATION; MECHANISTIC INSIGHT; CARBONYL-COMPOUNDS; ELECTRON-TRANSFER; ALPHA-KETOAMIDES; MOLECULAR-OXYGEN; TERMINAL ALKYNES; REACTION PATHWAY;
D O I
10.1002/ajoc.201500332
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed, aerobic, oxidative, C3-dicarbonylation of indoles has been realized directly from alpha-hydroxyketones, which serve as an efficient dicarbonylative reagent under mild conditions. The method is widely compatibility with various functional groups, offering a straightforward means to produce different heterocycle-substituted quinoxalines in excellent yields. These diverse fluorescent quinoxalines exhibited photophysical properties and solvatochromism in certain rules. Based on control experiments, a plausible reaction mechanism was proposed.
引用
收藏
页码:1370 / 1374
页数:5
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