Three-component reaction for the synthesis of imides enabled by electrochemical C(sp3)-H functionalization

被引:10
作者
Chu, Qiao [1 ]
Feng, Zhaoyue [1 ]
Zhang, Sumin [1 ]
Liu, Ping [1 ]
Sun, Peipei [1 ]
机构
[1] Nanjing Normal Univ, Jiangsu Collaborat Innovat Ctr Biomed Funct Mat, Sch Chem & Mat Sci, Jiangsu Prov Key Lab Mat Cycle Proc & Pollut Contr, Nanjing 210023, Peoples R China
基金
中国国家自然科学基金;
关键词
CONJUGATE ADDITION; CYCLIC IMIDES; NITRILES; AMIDES;
D O I
10.1039/d3gc02174b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An electrochemical three-component reaction cascade Mumm rearrangement was developed for the synthesis of imides. Commercially available aryl acids, nitriles, and alkylbenzenes were used as substrates without pre-functionalization, and the reactions were conducted under transition metal- and chemical oxidant-free conditions. Subsequent hydrolysis or reduction of the imide products could be easily achieved to synthesize amides, as well as primary or tertiary amines.
引用
收藏
页码:6728 / 6732
页数:5
相关论文
共 37 条
[1]   NHPI-Mediated Electrochemical α-Oxygenation of Amides to Benzimides [J].
Bai, Fang ;
Wang, Ning ;
Bai, Yinshan ;
Ma, Xiaowei ;
Gu, Chengzhi ;
Dai, Bin ;
Chen, Jianpeng .
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (05) :2985-2998
[2]   Three-Component Metal-Free Arylation of Isocyanides [J].
Basavanag, Unnamatla M. V. ;
Dos Santos, Aurelie ;
El Kaim, Laurent ;
Gamez-Montano, Rocio ;
Grimaud, Laurence .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) :7194-7197
[3]   Visible-Light-Induced Imide Synthesis through a Nitrile Ylide Formation/Trapping Cascade [J].
Cai, Bao-Gui ;
Yao, Wei-Zhong ;
Li, Lei ;
Xuan, Jun .
ORGANIC LETTERS, 2022, 24 (36) :6647-6652
[4]   Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis [J].
Cheng, Xu ;
Lei, Aiwen ;
Mei, Tian-Sheng ;
Xu, Hai-Chao ;
Xu, Kun ;
Zeng, Chengchu .
CCS CHEMISTRY, 2022, 4 (04) :1120-1152
[5]   Synthesis and biological activities of new checkpoint kinase 1 inhibitors structurally related to granulatimide [J].
Conchon, Elisabeth ;
Anizon, Fabrice ;
Aboab, Bettina ;
Prudhomme, Michelle .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (19) :4669-4680
[6]   Pestalazines and Pestalamides, Bioactive Metabolites from the Plant Pathogenic Fungus Pestalotiopsis theae [J].
Ding, Gang ;
Jiang, Lihua ;
Guo, Liangdong ;
Chen, Xulin ;
Zhang, Hua ;
Che, Yongsheng .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (11) :1861-1865
[7]   n-Type Organic and Polymeric Semiconductors Based on Bithiophene Imide Derivatives [J].
Feng, Kui ;
Guo, Han ;
Sun, Huiliang ;
Guo, Xugang .
ACCOUNTS OF CHEMICAL RESEARCH, 2021, 54 (20) :3804-3817
[8]   Highly enantioselective catalytic conjugate addition of N-heterocycles to α,β-unsaturated ketones and imides [J].
Gandelman, M ;
Jacobsen, EN .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2393-2397
[9]   Evaluation of Broad Anti-Coronavirus Activity of Autophagy-Related Compounds Using Human Airway Organoids [J].
Hashimoto, Rina ;
Tamura, Tomokazu ;
Watanabe, Yukio ;
Sakamoto, Ayaka ;
Yasuhara, Naoko ;
Ito, Hayato ;
Nakano, Masahiro ;
Fuse, Hiromitsu ;
Ohta, Akira ;
Noda, Takeshi ;
Matsumura, Yasufumi ;
Nagao, Miki ;
Yamamoto, Takuya ;
Takayama, Kazuo ;
Fukuhara, Takasuke .
MOLECULAR PHARMACEUTICS, 2023, 20 (04) :2276-2287
[10]   Ruthenium-Catalyzed Carbonylation at Ortho C-H Bonds in Aromatic Amides Leading to Phthalimides: C-H Bond Activation Utilizing a Bidentate System [J].
Inoue, Satoshi ;
Shiota, Hirotaka ;
Fukumoto, Yoshiya ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) :6898-+