Copper-catalyzed aerobic double functionalization of benzylic C(sp3)-H bonds for the synthesis of 3-hydroxyisoindolinones

被引:12
作者
Nozawa-Kumada, Kanako [1 ]
Matsuzawa, Yuta [1 ]
Ono, Kanako [1 ]
Shigeno, Masanori [1 ]
Kondo, Yoshinori [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Aoba Ku, 6-3 Aoba, Sendai, Miyagi 9808578, Japan
基金
日本学术振兴会;
关键词
C-H ACTIVATION; 3+2 ANNULATION; OXIDATION; AMINATION; DERIVATIVES; MOLECULES; KETIMINES; ALKYNES;
D O I
10.1039/d1cc02870g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A copper-catalyzed aerobic 3-hydroxyisoindolinone synthesis was developed via the benzylic double C(sp(3))-H functionalization of 2-alkylbenzamides. In this reaction, molecular oxygen was used as both an oxidant for C(sp(3))-H functionalization and an oxygen source. Our method can be extended to diverse benzylic C(sp(3))-H bonds and shows excellent functional group tolerance.
引用
收藏
页码:8604 / 8607
页数:4
相关论文
共 46 条
[41]   Different Behaviors of a Cu Catalyst in Amine Solvents: Controlling N and O Reactivities of Amide [J].
Yamane, Yu ;
Miyazaki, Koichiro ;
Nishikata, Takashi .
ACS CATALYSIS, 2016, 6 (11) :7418-7425
[42]   Eosin Y as a Redox Catalyst and Photosensitizer for Sequential Benzylic C-H Amination and Oxidation [J].
Yan, Dong-Mei ;
Zhao, Quan-Qing ;
Rao, Li ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (63) :16895-16901
[43]   Electrochemical Formation of N-Acyloxy Amidyl Radicals and Their Application: Regioselective Intramolecular Amination of sp2 and sp3 C-H Bonds [J].
Zhang, Sheng ;
Li, Lijun ;
Xue, Mengyu ;
Zhang, Ruike ;
Xu, Kun ;
Zeng, Chengchu .
ORGANIC LETTERS, 2018, 20 (12) :3443-3446
[44]   Copper-catalyzed aerobic asymmetric cross-dehydrogenative coupling of C(sp3)-H bonds driven by visible light [J].
Zhou, Kexu ;
Yu, Ying ;
Lin, Yu-Mei ;
Li, Yanjun ;
Gong, Lei .
GREEN CHEMISTRY, 2020, 22 (14) :4597-4603
[45]   Iodoarene-Catalyzed Stereospecific Intramolecular sp3 C-H Amination: Reaction Development and Mechanistic Insights [J].
Zhu, Chendan ;
Liang, Yong ;
Hong, Xin ;
Sun, Heqing ;
Sun, Wei-Yin ;
Houk, K. N. ;
Shi, Zhuangzhi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (24) :7564-7567
[46]   Copper-catalyzed oxidative carbon-heteroatom bond formation: a recent update [J].
Zhu, Xu ;
Chiba, Shunsuke .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (16) :4504-4523