Electrochemical construction of 2,5-diaryloxazoles via N-H and C(sp3)-H functionalization

被引：7

作者：

Li, Tong ^{[1
]}

Pan, Leping ^{[2
]}

Zhang, Yan ^{[1
]}

Su, Jihu ^{[3
]}

Li, Kai ^{[1
]}

Li, Kuiliang ^{[1
]}

Chen, Hu ^{[1
]}

Sun, Qi ^{[1
]}

Wang, Zhiyong ^{[1
]}

机构：

[1] Univ Sci & Technol China, Hefei Natl Ctr Phys Sci Microscale, Sch Chem & Mat Sci, Key Lab Precis & Intelligent Chem, Hefei 230026, Anhui, Peoples R China

[2] Anhui Univ Sci & Technol, Huainan 232001, Peoples R China

[3] Univ Sci & Technol China, Dept Modern Phys, CAS Key Lab Microscale Magnet Resonance, Hefei 230026, Peoples R China

来源：

CHINESE CHEMICAL LETTERS | 2024年 / 35卷 / 04期

关键词：

Electrochemical; Metal-free; Oxazole; Oxidant-free; ONE-POT SYNTHESIS; OXIDATIVE CYCLIZATION; OXAZOLES; CATALYST; CYCLOADDITION; DERIVATIVES; ESTERS;

D O I：

10.1016/j.cclet.2023.108897

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient N-H and C(sp3)-H functionalization of aryl ketones with benzylamines/amino acids was developed under mild conditions by virtue of anodic oxidation. A variety of functionalized 2,5diaryloxazoles were obtained with good to excellent yields. Moreover, some important natural products can be prepared by this method. The reaction features a broad substrate scope, scalability, metal -free and chemical oxidant -free. (c) 2024 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

引用

页数：6

共 42 条

[1] Electrochemical Synthesis of Polysubstituted Oxazoles from Ketones and Acetonitrile [J].

Bao, Liang ;

Liu, Chen ;

Li, Wenyi ;

Yu, Jiage ;

Wang, Min ;

Zhang, Yunfei .

ORGANIC LETTERS, 2022, :5762-5766

[2] Isocyano Enones: Addition-Cyclization Cascade to Oxazoles [J].

Chao, Allen ;

Armando Lujan-Montelongo, J. ;

Fleming, Fraser F. .

ORGANIC LETTERS, 2016, 18 (13) :3062-3065

[3] Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis [J].

Devi, Suman ;

Jyoti ;

Kiran ;

Wadhwa, Deepak ;

Sindhu, Jayant .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (26) :5163-5229

[4] Synthesis of 2,2,2-Trifluoroethyl Oxazoles, Oxazolines and Furans via Alkyne Oxytrifluoromethylation [J].

Dong, Jia-Jia ;

Zhang, Song-Lin .

ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (04) :795-800

[5] A simple and efficient approach to realize difunctionalization of arylketones with malonate esters via electrochemical oxidation [J].

Gao, Huihui ;

Zha, Zhenggen ;

Zhang, Zhenlei ;

Ma, Huanyue ;

Wang, Zhiyong .

CHEMICAL COMMUNICATIONS, 2014, 50 (39) :5034-5036

[6] A Direct Synthesis of Oxazoles from Aldehydes [J].

Graham, Thomas H. .

ORGANIC LETTERS, 2010, 12 (16) :3614-3617

[7] Electrochemical synthesis of 3-azido-indolines from amino-azidation of alkenes [J].

Guo, Shengping ;

Liu, Liyan ;

Hu, Kangfei ;

Sun, Qi ;

Zha, Zhenggen ;

Yang, Yu ;

Wang, Zhiyong .

CHINESE CHEMICAL LETTERS, 2021, 32 (03) :1033-1036

[8] Fluorocyclization of N-Propargylamides to Oxazoles by Electrochemically Generated ArIF2 [J].

Herszman, John D. ;

Berger, Michael ;

Waldvogel, Siegfried R. .

ORGANIC LETTERS, 2019, 21 (19) :7893-7896

[9] Metal-Free sp3 C-H Functionalization: PABS/I2-Promoted Synthesis of Polysubstituted Oxazole Derivatives from Arylethanones and 2-Amino-2-alkyl/arylacetic Acid [J].

Hu, Ting ;

Yan, Hao ;

Liu, Xingxing ;

Wu, Chaoyang ;

Fan, Yuxing ;

Huang, Jing ;

Huang, Guosheng .

SYNLETT, 2015, 26 (20) :2866-2869

[10] Practical Synthesis of Polysubstituted Imidazoles via Iodine- Catalyzed Aerobic Oxidative Cyclization of Aryl Ketones and Benzylamines [J].

Huang, Huawen ;

Ji, Xiaochen ;

Wu, Wanqing ;

Jiang, Huanfeng .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) :170-180

← 1 2 3 4 5 →