Trifluoromethylation of heterocycles via visible light photoredox catalysis

被引：189

作者：

Iqbal, Naeem ^{[1
]}

Choi, Sungkyu ^{[1
]}

Ko, Euna ^{[1
]}

Cho, Eun Jin ^{[1
]}

机构：

[1] Hanyang Univ, Dept Chem & Appl Chem, Ansan 426791, Kyeonggi Do, South Korea

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 15期

基金：

新加坡国家研究基金会;

关键词：

Visible light; Photoredox catalysis; Trifluoromethylation; Heterocycles; Ruthenium; C-H FUNCTIONALIZATION; OXIDATIVE TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; MEDICINAL CHEMISTRY; BORONIC ACIDS; ARYL; PHOTOCATALYSIS; FLUORINATION; BOND; CYCLOADDITIONS;

D O I：

10.1016/j.tetlet.2012.02.032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method has been developed for the visible light-induced trifluoromethylation of heterocyclic compounds. A variety of electron-rich heterocycles were transformed into trifluoromethylated products by using CF3I as the trifluoromethyl radical source and Ru(bpy)(3)Cl-2 as the photocatalyst under mild reaction conditions. This operationally simple and eco-friendly process can introduce trifluoromethyl groups without prefunctionalization. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2005 / 2008

页数：4

共 53 条

[1] Nucleophilic routes to selectively fluorinated aromatics
Adams, DJ
Clark, JH
[J]. CHEMICAL SOCIETY REVIEWS, 1999, 28 (04) : 225 - 231
[2] Andrews S. R., 2010, ANGEW CHEM, V122, P7432
[3] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV)
Ball, Nicholas D.
Kampf, Jeff W.
Sanford, Melanie S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 2878 - +
[4] The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates
Cho, Eun Jin
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2011, 13 (24) : 6552 - 6555
[5] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
Cho, Eun Jin
Senecal, Todd D.
Kinzel, Tom
Zhang, Yong
Watson, Donald A.
Buchwald, Stephen L.
[J]. SCIENCE, 2010, 328 (5986) : 1679 - 1681
[6] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids
Chu, Lingling
Qing, Feng-Ling
[J]. ORGANIC LETTERS, 2010, 12 (21) : 5060 - 5063
[7] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization
Condie, Allison G.
Gonzalez-Gomez, Jose C.
Stephenson, Corey R. J.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1464 - +
[8] Visible-light-mediated conversion of alcohols to halides
Dai, Chunhui
Narayanam, Jagan M. R.
Stephenson, Corey R. J.
[J]. NATURE CHEMISTRY, 2011, 3 (02) : 140 - 145
[9] Active trifluoromethylating agents from well-defined copper(I)-CF3 complexes
Dubinina, Galyna G.
Furutachi, Hideki
Vicic, David A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) : 8600 - +
[10] Visible Light-Mediated Intermolecular C-H Functionalization of Electron-Rich Heterocycles with Malonates
Furst, Laura
Matsuura, Bryan S.
Narayanam, Jagan M. R.
Tucker, Joseph W.
Stephenson, Corey R. J.
[J]. ORGANIC LETTERS, 2010, 12 (13) : 3104 - 3107

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