One pot and selective intermolecular aryl- and heteroaryl-trifluoromethylation of alkenes by photoredox catalysis

被引：102

作者：

Carboni, Aude ^{[1
]}

Dagousset, Guillaume ^{[1
]}

Magnier, Emmanuel ^{[2
]}

Masson, Geraldine ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] Univ Versailles St Quentin, UMR 8180, Inst Lavoisier Versailles, F-78035 Versailles, France

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 91期

关键词：

VISIBLE-LIGHT PHOTOCATALYSIS; C-H TRIFLUOROMETHYLATION; CHIRAL PHOSPHORIC-ACID; BOND FORMATION; ELECTROPHILIC TRIFLUOROMETHYLATION; SODIUM TRIFLUOROMETHANESULFINATE; MEDIATED TRIFLUOROMETHYLATION; UNACTIVATED ALKENES; ORGANIC-SYNTHESIS; CONSTRUCTION;

D O I：

10.1039/c4cc07066f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report herein the first photoredox-catalyzed intermolecular aryl- and heteroaryltrifluoromethylation of alkenes. Under the optimized conditions using Umemoto's reagent as a CF3 source, a wide range of styrenes can be readily difunctionalized, affording the corresponding trifluoromethylated adducts in up to 99% yield.

引用

页码：14197 / 14200

页数：4

共 27 条

[1] Trifluoromethylation of Alkenes by Visible Light Photoredox Catalysis
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JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (24) : 11383 - 11387
[2] Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis
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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 1099 - 1106
[3] Copper-mediated trifluoromethylation of aryl-, heteroaryl-, and vinyltrifluoroborates with Langlois' reagent
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RSC ADVANCES, 2014, 4 (13): : 6496 - 6499
[4] Synthesis of oxindoles through trifluoromethylation of N-aryl acrylamides by photoredox catalysis
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Liu, Zhiji
Zhang, Jinwang
Tian, Yu
Qin, Honggui
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[5] Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis
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[6] Intermolecular, redox-neutral azidoarylation of alkenes via photoredox catalysis
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Qin, Jian
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CHEMICAL COMMUNICATIONS, 2019, 55 (16) : 2336 - 2339
[7] Radical Fluoroalkylation of Aryl Alkenes with Fluorinated Sulfones by Visible- Light Photoredox Catalysis
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Ni Chuanfa
Wang Yunze
Kuang Cuiwen
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ACTA CHIMICA SINICA, 2017, 75 (01) : 105 - 109
[8] Visible light-induced aryltrifluoromethylation of hydroxy alkenes via radical trifluoromethylation-triggered aryl and heteroaryl migration
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Xu, Qian
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ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (14): : 2224 - 2228
[9] C5-selective trifluoromethylation of 8-amino quinolines via photoredox catalysis
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Yang, Li-Ming
Tian, Hai-Tao
An, Guang-Hui
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JOURNAL OF FLUORINE CHEMISTRY, 2019, 219 : 23 - 28
[10] Trifluoromethylation of aromatic alkenes by visible-light-driven photoredox catalysis: Direct conversion of alkenes to 3-trifluoromethyl-1-propenyl and 1,3-bis(trifluoromethyl)-1-propenyl derivatives
Asano, Masashi
Tomita, Ren
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JOURNAL OF FLUORINE CHEMISTRY, 2015, 179 : 83 - 88

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