Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis

被引：21
|
作者：
Sun, Bin [1 ,3 ]
Xu, Tengwei [2 ,3 ]
Zhang, Liang [2 ,3 ]
Zhu, Rui [2 ,3 ]
Yang, Jin [2 ,3 ]
Xu, Min [1 ,3 ]
Jin, Can [1 ,2 ,3 ]
机构：
[1] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China
[3] Zhejiang Univ Technol, Natl Engn Res Ctr Proc Dev Act Pharmaceut Ingredi, Hangzhou 310014, Zhejiang, Peoples R China
来源：
SYNLETT | 2020年 / 31卷 / 04期
基金：
中国国家自然科学基金;
关键词：
photocatalysis; C-H alkylation; NHP esters; regioselectivity; metal-free reactions; VISIBLE-LIGHT PHOTOREDOX; BOND FORMATION METHODOLOGY; C-H BONDS; DECARBOXYLATIVE ALKYLATION; COUPLING REACTION; IMIDAZOPYRIDINES; CYCLIZATION; IMIDAZOHETEROCYCLES; FUNCTIONALIZATION; CASCADE;
D O I：
10.1055/s-0039-1691567
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A visible-light-induced direct C-H alkylation of imidazo[1,2-a]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N-(NHP) esters as alkylation reagents. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) were tolerated in this protocol, giving the corresponding C-5-alkylated products in moderate to excellent yields. Mechanistic studies indicate that a radical decarboxylative coupling pathway was involved in this process.
引用
收藏
页码：363 / 368
页数：6
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