Construction of alkenyl-isoquinolinones through NHC-catalyzed remote C(sp3)-H acylation and cascade cyclization of benzamides and enals

被引：5
|
作者：
Zeng, Rong [1 ,2 ]
Xie, Chuan [2 ]
Xing, Jin-Dun [2 ]
Dai, Hai -Yu [2 ]
He, Mei-Hao [2 ]
Xu, Peng-Shuai [2 ]
Yang, Qi-Chun [2 ]
Han, Bo [1 ]
Li, Jun-Long [1 ]
机构：
[1] Chengdu Univ Tradit Chinese Med, State Key Lab Southwestern Chinese Med Resources, Chengdu 611137, Peoples R China
[2] Chengdu Univ, Sichuan Ind Inst Antibiot, Antibiot Res & Reevaluat Key Lab Sichuan Prov, Sch Pharm, Chengdu 610106, Peoples R China
来源：
TETRAHEDRON | 2023年 / 132卷
关键词：
N -heterocyclic carbene; Isoquinolinone; Radical acylation; Enal; SINGLE-ELECTRON-TRANSFER; ENANTIOSELECTIVE SYNTHESIS; BETA-HYDROXYLATION; CARBENE; ORGANOCATALYSIS; ACTIVATION; STRATEGY; ACIDS;
D O I：
10.1016/j.tet.2022.133239
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Available online A general and efficient method for constructing alkenyl-substituted isoquinolinones through N-heterocyclic carbene catalysis was described. The functionalization of benzamides with various enals proceeds smoothly through an N-center radical-mediated remote C (sp3)-H acylation and a cascade intramolecular hemiacetalization process. The newly designed thiazolium NHCs, exhibiting superior catalytic efficacy to activate the challenging enal substrates, is key to the success of this chemistry. This catalytic protocol further expands the generality of N-heterocyclic carbene radical catalysis.(c) 2022 Elsevier Ltd. All rights reserved.
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页数：9
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