Metal-free, Visible-Light-Induced Radical Trifluoromethylation/Cyclization of N-benzamides with CF3SO2Na to Synthesize CF3-Containing Isoquinoline-1,3-diones

被引：17

作者：

Wang, Shaowei ^{[1
,2
]}

Dai, Peng ^{[1
,2
]}

Yan, Zhichao ^{[1
,2
]}

Wang, Youjia ^{[1
,2
]}

Shao, Jiaxuan ^{[1
,2
]}

Wu, Yanhui ^{[1
,2
]}

Deng, Chao ^{[1
,2
]}

Zhang, Weihua ^{[1
,2
]}

机构：

[1] Nanjing Agr Univ, Coll Sci, Jiangsu Key Lab Pesticide Sci, Nanjing 210095, Jiangsu, Peoples R China

[2] Nanjing Agr Univ, Coll Sci, Dept Chem, Nanjing 210095, Jiangsu, Peoples R China

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 35期

关键词：

antifungal activity; Isoquinoline-1; 3-diones; Photo-Induced; Trifluoromethylation; FLUORINATED SULFONES; CATALYTIC HYDROTRIFLUOROMETHYLATION; SELECTIVE INHIBITORS; AROMATIC-ALDEHYDES; ALKENES; DIFUNCTIONALIZATION; CYCLIZATION; CARBOTRIFLUOROMETHYLATION; OXYTRIFLUOROMETHYLATION; FUNCTIONALIZATION;

D O I：

10.1002/slct.201902545

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel visible-light-induced radical cascade trifluoromethylation/cyclization of N-benzamides with CF3SO2Na has been achieved. This protocol provides an efficient strategy for the synthesis of CF3-containing isoquinoline-1,3-diones under mild reaction conditions. The reaction features metal-free, air oxidation, CF3SO2Na as CF3 source, additives free and operational simplicity. Moreover, the representative products displayed significant potencial antifungal activities in vitro.

引用

页码：10329 / 10333

页数：5

共 30 条

[1] Synthesis of CF2H-containing isoquinoline-1,3-diones through metal-free, visible-light and air-promoted radical difluoromethylation/cyclization of N-benzamides
Shao, Jiaxuan
Wang, Youjia
Chen, Silu
Wang, Shaowei
Wu, Yanhui
Li, Xulian
Zhang, Weihua
Deng, Chao
TETRAHEDRON, 2021, 79
[2] Visible-light induced di- and trifluoromethylation of N-benzamides with fluorinated sulfones for the synthesis of CF2H/CF3-containing isoquinolinediones
Zou, Guanglong
Wang, Xuelin
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (41) : 8748 - 8754
[3] Visible-light-induced radical cyclization of N-allylbenzamides with CF3SO2Na to trifluoromethylated dihydroisoquinolinones in water at room temperature
Zou, Long
Li, Pinhua
Wang, Bin
Wang, Lei
GREEN CHEMISTRY, 2019, 21 (12) : 3362 - 3369
[4] Metal-free oxidative trifluoromethylation of indoles with CF3SO2Na on the C2 position
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[5] Visible-light-promoted olefinic trifluoromethylation of enamides with CF3SO2Na
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Xiang, Haoyue
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ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (34) : 7475 - 7479
[6] Base-promoted cascade radical difluoroalkylation/cyclization of acrylamides for the synthesis of CF2-containing oxindoles and isoquinoline-1,3-diones
Ma, Shidi
Zhou, Pengsheng
Fan, Xu
Li, Dianjun
Yang, Jinhui
TETRAHEDRON LETTERS, 2022, 102
[7] Visible-Light-Induced DDQ-Catalyzed Fluorocarbamoylation Using CF3SO2Na and Oxygen
Cho, Huijeong
Jang, Seonga
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Cha, Dohoon
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ORGANIC LETTERS, 2023, 25 (48) : 8558 - 8563
[8] Visible-Light-Induced Trifluoromethylation of N-Aryl Acrylamides: A Convenient and Effective Method To Synthesize CF3-Containing Oxindoles Bearing a Quaternary Carbon Center
Xu, Pan
Xie, Jin
Xue, Qicai
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CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (42) : 14039 - 14042
[9] Visible-light-induced Pd-catalyzed ortho-trifluoromethylation of acetanilides with CF3SO2Na under ambient conditions in the absence of an external photocatalyst
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[10] Visible-light-induced photocatalytic oxytrifluoromethylation of N-allylamides for the synthesis of CF3-containing oxazolines and benzoxazines
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CHEMICAL COMMUNICATIONS, 2015, 51 (17) : 3537 - 3540

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