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

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 73期

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

页码：10634 / 10636

页数：3

共 50 条

[21] Iron-Mediated Oxidative C-H Alkylation of S,S-Functionalized Internal Olefins via C(sp2)-H/C(sp3)-H Cross-Coupling [J].

Wang, Quannan ;

Lou, Jiang ;

Wu, Ping ;

Wu, Kaikai ;

Yu, Zhengkun .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (17) :2981-2998

[22] Atroposelective sp3 C-H Coupling for Kinetic Resolution of Thioanilide Atropisomers [J].

Jiang, Hua-Jie ;

Geng, Rui-Long ;

Wei, Jia-Hui ;

Gong, Liu-Zhu .

CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (12) :3269-3276

[23] Photocatalytic Methylation of Nonactivated sp3 and sp2 C-H Bonds Using Methanol on GaN [J].

Liu, Mingxin ;

Qiu, Zihang ;

Tan, Lida ;

Rashid, Roksana T. ;

Chu, Sheng ;

Cen, Yunen ;

Luo, Ziling ;

Khaliullin, Rustam Z. ;

Mi, Zetian ;

Li, Chao Jun .

ACS CATALYSIS, 2020, 10 (11) :6248-6253

[24] Copper-Mediated Dehydrogenative C(sp3)-H Borylation of Alkanes [J].

Sang, Ruocheng ;

Han, Wangyujing ;

Zhang, Hanwen ;

Saunders, Carla M. ;

Noble, Adam ;

Aggarwal, Varinder K. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (28) :15207-15217

[25] Copper-catalyzed phosphorylation of sp2 C-H bonds [J].

Wang, Shan ;

Guo, Rui ;

Wang, Gao ;

Chen, Shan-Yong ;

Yu, Xiao-Qi .

CHEMICAL COMMUNICATIONS, 2014, 50 (84) :12718-12721

[26] Nickel-Catalyzed C(sp2)-H/C(sp3)-H Oxidative Coupling of Indoles with Toluene Derivatives [J].

Soni, Vineeta ;

Khake, Shrikant M. ;

Punji, Benudhar .

ACS CATALYSIS, 2017, 7 (06) :4202-4208

[27] A straightforward access to guaiazulene derivatives using palladium-catalysed sp2 or sp3 C-H bond functionalisation [J].

Zhao, Liqin ;

Bruneau, Christian ;

Doucet, Henri .

CHEMICAL COMMUNICATIONS, 2013, 49 (49) :5598-5600

[28] Iron- Catalyzed C( sp2)-H and C( sp3) -H Arylation by Triazole Assistance [J].

Gu, Qing ;

Al Mamari, Hamad H. ;

Graczyk, Karolina ;

Diers, Emelyne ;

Ackermann, Lutz .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (15) :3868-3871

[29] Transition-Metal-Free, Intramolecular Oxidative Coupling of C(sp3)-B with C(sp2)-H [J].

Dan, Tingting ;

Liu, Yuling ;

Li, Lai ;

Yang, Wenwen ;

Yang, Mingyu ;

Shi, Zhangjie .

ORGANIC LETTERS, 2025, 27 (22) :5737-5743

[30] Iodine-Mediated C-H Functionalization of sp, sp2, and sp3 Carbon: A Unified Multisubstrate Domino Approach for Isatin Synthesis [J].

Satish, Gandhesiri ;

Polu, Ashok ;

Ramar, Thangeswaran ;

Ilangovan, Andivelu .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (10) :5167-5175

← 1 2 3 4 5 →