Bromide-promoted cascade annulation of isocyanobiaryls with aldehydes through photoredox catalysis

被引:0
|
作者
Gan, Mengran [1 ]
Wu, Xiaoting [1 ]
Ji, Xiaochen [1 ,2 ]
Huang, Huawen [1 ,2 ]
机构
[1] Xiangtan Univ, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environmentally Friendly Chem & Applicat, Minist Educ,Coll Chem, Xiangtan 411105, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China
关键词
MINISCI REACTION; CYCLIZATION; ISOCYANIDES; PATHWAY; OXIDE;
D O I
10.1039/d4ob02085e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a cascade annulation of readily available isocyanobiaryls with simple aldehydes via photoredox catalysis, providing a straightforward approach towards valuable 6-hydroxyalkylated phenanthridines. Mechanistic studies indicated the generation of a key acyl radical from aldehydes by hydrogen atom abstraction with a bromine radical. This protocol exhibits exceptional chemoselectivity, excellent tolerance of various functional groups and mild reaction conditions. Its synthetic utility was demonstrated by a gram-scale reaction and various facile manipulations of the free hydroxyl group to furnish diverse phenanthridine derivatives.
引用
收藏
页码:2101 / 2105
页数:5
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