Photocatalyst-Free Regioselective C-H Thiocyanation of 4-Anilinocoumarins under Visible Light

被引：96

作者：

Li, Guoqing ^{[2
]}

Yan, Qiuli ^{[1
,2
]}

Gong, Xueqin ^{[2
]}

Dou, Xiaomeng ^{[3
]}

Yang, Daoshan ^{[1
,2
]}

机构：

[1] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, State Key Lab Base Ecochem Engn, Zhengzhou Rd 53, Qingdao 266042, Shandong, Peoples R China

[2] Qufu Normal Univ, Sch Chem & Chem Engn, Yulong Rd 57, Qufu 273165, Peoples R China

[3] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Taoyuan Rd 1, Xiangtan 411201, Peoples R China

来源：

ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2019年 / 7卷 / 16期

基金：

中国国家自然科学基金;

关键词：

Photocatalyst-free; C-H thiocyanation; Visible light; Enaminone; Sustainable synthetic chemistry; QUINOLINE N-OXIDES; PHOTOREDOX CATALYSIS; BOND FUNCTIONALIZATION; AMMONIUM THIOCYANATE; C-3; THIOCYANATION; INDOLES; ACTIVATION; COUMARINS; DERIVATIVES; ALKYLATION;

D O I：

10.1021/acssuschemeng.9b02511

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the present study, we describe the successful development of a novel and efficient C(sp(2))-H thiocyanation reaction of electron-rich heteroarenes and arenes with readily available ammonium thiocyanate under visible light exposure. Most importantly, the reaction proceeded smoothly without addition of any photocatalyst or strong oxidant, ultimately minimizing the production of chemical waste. The advantages of this reaction met the requirements of green and sustainable synthetic chemistry and may be widely used in organic synthesis and pharmaceutical chemistry.

引用

页码：14009 / 14015

页数：13

共 50 条

[41] Copper-Catalyzed Regioselective Direct C-H Thiolation and Thiocyanation of Uracils
Noikham, Medena
Yotphan, Sirilata
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (16) : 2759 - 2766
[42] Visible Light-Promoted, Photocatalyst-Free C(sp2)-H Bond Functionalization of Indolizines via EDA Complexes
Mane, Kishor D.
Rupanawar, Bapurao D.
Suryavanshi, Gurunath
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (18)
[43] A g-C3N4/rGO nanocomposite as a highly efficient metal-free photocatalyst for direct C-H arylation under visible light irradiation
Cai, Xiaohui
Liu, Hanwen
Zhi, Lihua
Wen, Huang
Yu, Ailing
Li, Lianhua
Chen, Fengjuan
Wang, Baodui
RSC ADVANCES, 2017, 7 (73): : 46132 - 46138
[44] "Metal-free" electrooxidative C-H thiocyanation of arenes
Kokorekin, V. A.
Mel'nikova, E. I.
Yaubasarova, R. R.
Gorpinchenko, N. V.
Petrosyan, V. A.
RUSSIAN CHEMICAL BULLETIN, 2019, 68 (11) : 2140 - 2141
[45] Visible-Light-Mediated, Organophotocatalytic C-H Thiocyanation of Pyrazolo[1,5-a]pyrimidines
Pattanayak, Paramita
Satyanarayana, Appanapalli N. V.
Chatterjee, Tanmay
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13215 - 13223
[46] Visible Light-Assisted Photocatalyst-Free Tandem Sulfonylation/Cyclization for the Synthesis of Oxindoles
Wu, Xiaoting
Zhao, Feng
Ji, Xiaochen
Huang, Huawen
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) : 4323 - 4331
[47] Visible-light promoted photocatalyst-free aerobic α-oxidation of tertiary amines to amides
Xie, Xinpeng
Guo, Xuan
Qiao, Kaikai
Shi, Lei
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (41) : 8031 - 8036
[48] Photocatalyst-free, Visible Light Driven, Gold Promoted Suzuki Synthesis of (Hetero)biaryls
Sauer, Christopher
Liu, Yang
De Nisi, Assunta
Protti, Stefano
Fagnoni, Maurizio
Bandini, Marco
CHEMCATCHEM, 2017, 9 (24) : 4456 - 4459
[49] Metal- and photocatalyst-free approach to visible-light-induced acylation of quinoxalinones
Niwetmarin, Worawat
Saesian, Naiyana
Saruengkhanphasit, Rungroj
Eurtivong, Chatchakorn
Thasana, Nopporn
Ruchirawat, Somsak
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (29) : 5924 - 5929
[50] A functionalized ruthenium-graphene nanosheet photocatalyst for highly regioselective visible light driven C-H arylation of imidazo-pyrimidines
Yadav, Rajesh K.
Kumar, Abhishek
Park, No-Joong
Yadav, Dolly
Kim, Jae Young
Baeg, Jin-Ook
SUSTAINABLE ENERGY & FUELS, 2019, 3 (12): : 3324 - 3328

← 1 2 3 4 5 →