Synthesis of Highly Functionalized Polycyclic Quinoxaline Derivatives Using Visible-Light Photoredox Catalysis

被引：151

作者：

He, Zhi ^{[1
]}

Bae, Minwoo ^{[1
]}

Wu, Jie ^{[1
]}

Jamison, Timothy F. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 52期

关键词：

flow chemistry; heterocycles; isocyanide; photochemistry; radicals; ONE-POT SYNTHESIS; C BOND FORMATION; METAL-FREE; CONTINUOUS-FLOW; PHENANTHRIDINES; CYCLIZATION; 2-ISOCYANOBIPHENYLS; ISOCYANIDES; PHOTOCHEMISTRY; ANNULATION;

D O I：

10.1002/anie.201408522

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A mild and facile method for preparing highly functionalized pyrrolo[1,2-a]quinoxalines and other nitrogen-rich heterocycles, each containing a quinoxaline core or an analogue thereof, has been developed. The novel method features a visible-light-induced decarboxylative radical coupling of ortho-substituted arylisocyanides and radicals generated from phenyliodine(III) dicarboxylate reagents and exhibits excellent functional group compatibility. A wide range of quinoxaline heterocycles have been prepared. Finally, a telescoped preparation of these polycyclic compounds by integration of the in-line isocyanide formation and photochemical cyclization has been established in a three-step continuous-flow system.

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收藏

页码：14451 / 14455

页数：5

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