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

[31] CONDENSED HETEROCYCLIC LACTAMS .1. STUDY ON THE CYCLIZATION METHODS RESULTING IN 4-ARYL-3,4-DIHYDROQUINOLIN-2(1H)-ONES
HAZAI, L
DEAK, G
SOHAR, P
TOTH, G
TAMAS, J
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (04) : 919 - 922
[32] Effect of substituents on 3(S)-amino-1-hydroxy-3,4-dihydroquinolin-2(1H)-one: a DFT study
Jerónimo Lira
Diego Valencia
Haruna Barazorda
Jaime Cárdenas-Garcia
Badhin Gómez
Theoretical Chemistry Accounts, 2019, 138
[33] Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives
Gurskaya, Larisa Yu.
Belyanskaya, Diana S.
Ryabukhin, Dmitry S.
Nilov, Denis I.
Boyarskaya, Irina A.
Vasilyev, Aleksander V.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2016, 12 : 950 - 956
[34] Effect of substituents on 3(S)-amino-1-hydroxy-3,4-dihydroquinolin-2(1H)-one: a DFT study
Lira, Jeronimo
Valencia, Diego
Barazorda, Haruna
Cardenas-Garcia, Jaime
Gomez, Badhin
THEORETICAL CHEMISTRY ACCOUNTS, 2019, 138 (01)
[35] Synthesis and antiplatelet-activity evaluation of α-methylidene-γ-butyrolactones bearing 3,4-dihydroquinolin-2(1H)-one moieties
Tzeng, CC
Chen, IL
Chen, YL
Wang, TC
Chang, YL
Teng, CM
HELVETICA CHIMICA ACTA, 2000, 83 (02) : 349 - 358
[36] Metal-Free Synthesis of 3,4-Dihydroquinolin-2(1H)-Ones Via Cascade Oxidative Decarbonylative Radical Alkylation/Cyclization Of Cinnamamides with Aliphatic Aldehydes
Xu, Xuemei
Luo, Zaigang
Liu, Chen-Fu
Wang, Xiuxiu
Deng, Liangdan
Gao, Jie
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (10) : 1903 - 1906
[37] 5,6,8-trichloro-4-phenyl-3,4-dihydroquinolin-2(1H)-one
Thirumurugan, R
Raj, SSS
Murugan, P
Ramakrishnan, VT
Chacko, KK
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1997, 53 : 1862 - 1864
[38] 7-Amino-4-hydroxy-4-trifluoromethyl-3,4-dihydroquinolin-2(1H)-one
Qin, Yuan
Xi, Haitao
Chen, Liang
Sun, Xiaoqiang
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2616 - +
[39] Generation of stereodefined (Z)-3,4-dihydronaphthalen-1(2H)-ones via copper-catalyzed annulation-cyanotrifluoromethylation of 1,7-enynes
Ji, Wen-Zhe
Shi, Hao-Nan
Hao, Wen-Juan
Wei, Ping
Tu, Shu-Jiang
Jiang, Bo
TETRAHEDRON LETTERS, 2021, 64
[40] Fe-Catalyzed decarbonylative cascade reaction of N-aryl cinnamamides with aliphatic aldehydes to construct 3,4-dihydroquinolin-2(1H)-ones
Gao, Ru-Xin
Luan, Xin-Qi
Xie, Zi-Yi
Yang, Luo
Pei, Yong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (21) : 5262 - 5268

← 1 2 3 4 5 →