Copper-mediated C-H(sp2)/C-H(sp3) coupling of benzoic acid derivatives with ethyl cyanoacetate: an expedient route to an isoquinolinone scaffold

被引:52
作者
Zhu, Wei [1 ]
Zhang, Dengyou [1 ]
Yang, Nan [1 ]
Liu, Hong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, Key Lab Receptor Res, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H BONDS; DIRECT FUNCTIONALIZATION; DIRECTING GROUP; ACTIVATION; ARYL; ARYLATION; ARENE; ALKALOIDS; HALIDES;
D O I
10.1039/c4cc03837a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile, copper-mediated, direct C-H(sp(2))/C-H(sp(3)) bond coupling of benzoic acid derivatives with ethyl cyanoacetate by the deployment of an 8-aminoquinoline moiety as a bidentate directing group is disclosed. Such a unique transformation provides a new strategy for the construction of an isoquinolinone scaffold as one of the privileged cores.
引用
收藏
页码:10634 / 10636
页数:3
相关论文
共 50 条
[41]   Cooperative C(sp3)-H and C(sp2)-H Activation of 2-Ethylpyridines by Copper and Rhodium: A Route toward Quinolizinium Salts [J].
Luo, Ching-Zong ;
Gandeepan, Parthasarathy ;
Wu, Yun-Ching ;
Tsai, Chia-Hung ;
Cheng, Chien-Hong .
ACS CATALYSIS, 2015, 5 (08) :4837-4841
[42]   Cobalt-Catalyzed, Aminoquinoline-Directed Coupling of sp2 C-H Bonds with Alkenes [J].
Grigorjeva, Liene ;
Daugulis, Olafs .
ORGANIC LETTERS, 2014, 16 (17) :4684-4687
[43]   Non-chelation-assisted Pd-catalysed novel sp3 C-H/sp2 C-H intermolecular oxidative coupling reaction: one-pot formation of new 5 benzyl fluorenone [J].
Sun, Qun ;
Liu, Li ;
Jiang, Hongxia ;
Chen, Shu ;
Liu, Jianqun .
TETRAHEDRON LETTERS, 2022, 104
[44]   Pd(II)-Catalyzed Olefination of sp3 C-H Bonds [J].
Wasa, Masayuki ;
Engle, Keary M. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3680-+
[45]   Manganese/cobalt-catalyzed oxidative C(sp3)-H/C(sp3)-H coupling: a route to α-tertiary β-arylethylamines [J].
Tan, Meiling ;
Li, Kaizhi ;
Yin, Jiangliang ;
You, Jingsong .
CHEMICAL COMMUNICATIONS, 2018, 54 (10) :1221-1224
[46]   Alkali-amide-catalyzed divergent sp2 and sp3 C-H bonds alkylation of alkylthiophenes with alkenes [J].
Luo, Yan-Long ;
Du, Hui-Zhen ;
Guan, Bing-Tao .
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (15) :4171-4176
[47]   Understanding the Effects of Bidentate Directing Groups: A Unified Rationale for sp2 and sp3 C-H Bond Activations [J].
Tang, Hao ;
Huang, Xu-Ri ;
Yao, Jiannian ;
Chen, Hui .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09) :4672-4682
[48]   Iron-Catalyzed C(sp2)H and C(sp3)H Methylations of Amides and Anilides [J].
Graczyk, Karolina ;
Haven, Tobias ;
Ackermann, Lutz .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (24) :8812-8815
[49]   Copper-Mediated Sulfonylation of Aryl C(sp2)-H Bonds with Sodium and Lithium Sulfinates [J].
Liang, Shuai ;
Liu, Nai-Wei ;
Manolikakes, Georg .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (01) :159-163
[50]   Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp2)-H and C(sp3)-H Bonds at δ- and ε-Positions [J].
Wang, Chao ;
Chen, Changpeng ;
Zhang, Jingyu ;
Han, Jian ;
Wang, Qian ;
Guo, Kun ;
Liu, Pei ;
Guan, Mingyu ;
Yao, Yingming ;
Zhao, Yingsheng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) :9884-9888