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.

引用

页数：9

共 50 条

[21] Ni-Catalyzed Remote Radical/Cross-Electrophile Coupling Cascade for Selective C(sp3)-H Arylation
Wen, Ya-Ting
Kong, Xiang-Tao
Liu, Hong-Chao
Wang, Cui-Tian
Wei, Wan-Xu
Wang, Bin
Liu, Xue-Yuan
Liang, Yong-Min
ORGANIC LETTERS, 2022, 24 (12) : 2399 - 2403
[22] Palladium-Catalyzed Remote C(sp3)-H Arylation of 3-Pinanamine
Cui, Wei
Chen, Shengwei
Wu, Jia-Qiang
Zhao, Xin
Hu, Wenhui
Wang, Honggen
ORGANIC LETTERS, 2014, 16 (16) : 4288 - 4291
[23] Undecorated Cu(OAc)2-Catalyzed C(sp3)-C(sp3) Bond Formation through para-Hydroxy Group Triggered Remote Benzylic C(sp3)-H Bond Functionalization
Huang, Jian-Gang
Guo, Ying
Li, Yu-Dan
Liu, Hong-Wei
Liao, Dao-Hua
Ji, Ya-Fei
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (24) : 5334 - 5338
[24] Pd-Catalyzed Cascade Heck/C(sp3)-H Activation for Spirocyclopropyl Oxindoles
Hafeez, Saleem
Sharma, Ruchi
Jain, Swati
Sihag, Naveen
Bhartiya, Hemaang
Singh, Jitendra
Reddy, S. Rajagopala
Yadav, M. Ramu
ORGANIC LETTERS, 2024, 26 (24) : 5069 - 5073
[25] Allylic C(sp3)-C(sp3) Bond Formation Through Pd-Catalyzed C(sp3)-H Activation of Alkenes and 1,4-Dienes
Muzart, Jacques
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (14) : 2268 - 2288
[26] Iron-Catalyzed C(sp3)-C(sp3) Bond Formation through C(sp3)-H Functionalization: A Cross-Coupling Reaction of Alcohols with Alkenes
Zhang, Shu-Yu
Tu, Yong-Qiang
Fan, Chun-An
Zhang, Fu-Min
Shi, Lei
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) : 8761 - 8765
[27] Enantioselective functionalization of unactivated C(sp3)–H bonds through copper-catalyzed diyne cyclization by kinetic resolution
Yang-Bo Chen
Li-Gao Liu
Zhe-Qi Wang
Rong Chang
Xin Lu
Bo Zhou
Long-Wu Ye
Nature Communications, 15
[28] Enantioselective functionalization of unactivated C(sp3)-H bonds through copper-catalyzed diyne cyclization by kinetic resolution
Chen, Yang-Bo
Liu, Li-Gao
Wang, Zhe-Qi
Chang, Rong
Lu, Xin
Zhou, Bo
Ye, Long-Wu
NATURE COMMUNICATIONS, 2024, 15 (01)
[29] Rhodium(III)-Catalyzed Allylic C(sp3)-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles
Archambeau, Alexis
Rovis, Tomislav
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (45) : 13337 - 13340
[30] Copper-Catalyzed, Interrupted Remote Fluoromethylthiolation of Unactivated C(sp3)-H Bonds
Yu, Fan
Wang, Wengui
Wang, Shoufeng
ORGANIC LETTERS, 2024, 26 (10) : 2068 - 2072

← 1 2 3 4 5 →