Photoredox-Catalzyed Halo-trifluoromethylation of 1,7-Enynes for Synthesis of 3,4-Dihydroquinolin-2(1H)-ones

被引：38

作者：

Yuan, Xin ^{[1
,2
]}

Zheng, Ming-Wei ^{[1
,2
]}

Di, Zhe-Chen ^{[1
]}

Cui, Yu-Sheng ^{[1
]}

Zhuang, Kai-Qiang ^{[1
]}

Qin, Long-Zhou ^{[1
]}

Fang, Zheng ^{[1
]}

Qiu, Jiang-Kai ^{[1
]}

Li, Guigen ^{[2
,3
]}

Guo, Kai ^{[1
]}

机构：

[1] Nanjing Tech Univ, Biotechnol & Pharmaceut Engn, Nanjing 211816, Jiangsu, Peoples R China

[2] Nanjing Univ, Inst Chem & Biomed Sci, Nanjing 210093, Jiangsu, Peoples R China

[3] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 08期

基金：

中国国家自然科学基金;

关键词：

photoredox; halo-trifluoromethylation; 1; 7-enynes; radical pathway; BENZENE-TETHERED 1,7-ENYNES; VISIBLE-LIGHT PHOTOCATALYSIS; RADICAL CYCLIZATION; BETA-AMINOPHOSPHONATES; CASCADE CYCLIZATION; CATALYSIS; PERFLUOROALKYLATION; FUNCTIONALIZATION; FLUORINATION; N-ENYNES;

D O I：

10.1002/adsc.201801681

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient photoredox-catalyzed halo-trifluoromethylation reaction of 1,7-enynes has been developed under mild conditions. This photocatalytic protocol provides an efficient and functional strategy leading to CF3- and halogen-containing 3,4-dihydroquinolin-2(1H)-ones from a wide range of 1,7-enynes through two different radical pathways. The reaction mechanism was proposed based on the control experiments.

引用

页码：1835 / 1845

页数：11

共 50 条

[1] Metal-Free Radical-Triggered Selenosulfonation of 1,7-Enynes for the Rapid Synthesis of 3,4-Dihydroquinolin-2(1H)-ones in Batch and Flow
Qiu, Jiang-Kai
Shan, Cheng
Wang, De-Cai
Wei, Ping
Jiang, Bo
Tu, Shu-Jiang
Li, Guigen
Guo, Kai
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (24) : 4332 - 4339
[2] Metal-Free Radical Haloazidation of Benzene-Tethered 1,7-Enynes Leading to Polyfunctionalized 3,4-Dihydroquinolin-2(1H)-ones
Wang, Ai-Fang
Zhu, Yi-Long
Wang, Shu-Liang
Hao, Wen-Juan
Li, Guigen
Tu, Shu-Jiang
Jiang, Bo
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (03): : 1099 - 1105
[3] Synthesis of trifluoromethylated 3,4-dihydroquinolin-2(1H)-ones via a photo-induced radical cyclization of benzene-tethered 1,7-enynes with Togni reagent
An, Yuanyuan
Kuang, Yunyan
Wu, Jie
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (08): : 994 - 998
[4] Photoredox One-Pot Synthesis of 3,4-Dihydroquinolin-2(1 H )-ones
He, Jing-Yao
Bai, Qi-Fan
Li, Xuewen
Shou, Jianxin
Feng, Gaofeng
SYNLETT, 2022, 33 (07) : 679 - 683
[5] Benzothiazines in synthesis: Synthesis of enantiomerically pure 3,4-dihydroquinolin-2(1H)-ones
Harmata, Michael
Hong, Xuechuan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
[6] Generation of Carbamoyl Radicals and 3,4-Dihydroquinolin-2(1H )-ones Enabled by Iron Photoredox Catalysis
Fu, Yanhua
Zhang, Chao
Cai, Tao
Feng, Gaofeng
SYNLETT, 2025, 36 (02) : 166 - 170
[7] A new cascade halosulfonylation of 1,7-enynes toward 3,4-dihydroquinolin-2(1H)-ones via sulfonyl radical-triggered addition/6-exo-dig cyclization
Zhu, Yi-Long
Jiang, Bo
Hao, Wen-Juan
Wang, Ai-Fang
Qiu, Jiang-Kai
Wei, Ping
Wang, De-Cai
Li, Guigen
Tu, Shu-Jiang
CHEMICAL COMMUNICATIONS, 2016, 52 (09) : 1907 - 1910
[8] Oxidative bicyclization of N-tethered 1,7-enynes toward polycyclic 3,4-dihydroquinolin-2(1H)-ones via site-selective decarboxylative C(sp3)-H functionalization
Li, Jie
Hao, Wen-Juan
Zhou, Peng
Zhu, Yi-Long
Wang, Shu-Liang
Tu, Shu-Jiang
Jiang, Bo
RSC ADVANCES, 2017, 7 (16): : 9693 - 9703
[9] Carbamoyl Radicals via Photoredox Decarboxylation of Oxamic Acids in Aqueous Media: Access to 3,4-Dihydroquinolin-2(1H)-ones
Bai, Qa-Fan
Jin, Chengan
He, Jing-Yao
Feng, Gaofeng
ORGANIC LETTERS, 2018, 20 (08) : 2172 - 2175
[10] Novel synthesis and cytotoxic activity of 1,4-disubstituted 3-methylidene-3,4-dihydroquinolin-2(1H)-ones
Pieta, Marlena
Kedzia, Jacek
Janecka, Anna
Pomorska, Dorota K.
Rozalski, Marek
Krajewska, Urszula
Janecki, Tomasz
RSC ADVANCES, 2015, 5 (95): : 78324 - 78335

← 1 2 3 4 5 →