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
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.
引用
收藏
页码:14451 / 14455
页数:5
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