2-oxo-2H-chromen-7-olate Catalyzed C-C and C-N Bond Formations in Visible Light

被引：0
|
作者：
Dixit, Vikas [1 ]
Sharma, Shruti [1 ]
Jain, Nidhi [1 ]
机构：
[1] Indian Inst Technol Delhi, Dept Chem, Delhi 110016, India
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2025年
关键词：
7-hydroxycoumarin; 2-oxo-2<italic>H</italic>-chromen-7-olate; hypervalent iodonium ylides; arylation; hydroxy-arylation; alkylation; amination; ROOM-TEMPERATURE; METAL-FREE; PHOTOREDOX; ARYLATION; CHLORIDES; OXYARYLATION; ALKYLATION; AMINES; SALTS;
D O I：
10.1002/ajoc.202400684
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
7-hydroxycoumarin is a naturally occurring compound with useful biological and fluorescent properties. In this work, we demonstrate a base-assisted photoactivation of 7-hydroxycoumarin in blue LED and its potential in enabling C-C and C-N bond formations. 7-hydroxycoumarin, on deprotonation with Cs2CO3 forms 2-oxo-2H-chromen-7-olate which exhibits photoreductant properties and mediates arylation and hydroxyarylation using hypervalent iodonium ylides; alkylation using N-hydroxyphthalimide esters; and amination with primary and secondary amines. The strategy does not require any additional metal or organic dye-based photocatalyst and offers a good functional group tolerance giving the C-C and C-N coupled products in moderate to good yields.
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页数：8
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