Metal-free electrochemical fluorodecarboxylation of aryloxyacetic acids to fluoromethyl aryl ethers

被引：51

作者：

Berger, Michael ^{[1
]}

Herszman, John D. ^{[1
]}

Kurimoto, Yuji ^{[1
,2
]}

de Kruijff, Goswinus H. M. ^{[1
]}

Schuell, Aaron ^{[1
,3
]}

Ruf, Sven ^{[3
]}

Waldvogel, Siegfried R. ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Dept Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

[2] Okayama Univ, Grad Sch Nat Sci & Technol, Okayama 7008530, Japan

[3] Sanofi Aventis Deutschland GmbH, D-65926 Frankfurt, Germany

来源：

CHEMICAL SCIENCE | 2020年 / 11卷 / 23期

关键词：

ALPHA-FLUORINATED ETHERS; DECARBOXYLATIVE FLUORINATION; CARBOXYLIC-ACIDS; THIOETHERS; CHEMISTRY; REAGENTS; AMINES; TRENDS;

D O I：

10.1039/d0sc02417a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Electrochemical decarboxylation of aryloxyacetic acids followed by fluorination provides easy access to fluoromethyl aryl ethers. This electrochemical fluorodecarboxylation offers a sustainable approach with electric current as traceless oxidant. Using Et3N center dot 5HF as fluoride source and as supporting electrolyte, this simple electrosynthesis affords various fluoromethoxyarenes in yields up to 85%.

引用

页码：6053 / 6057

页数：5

共 51 条

[1] Fluorine in medicinal chemistry [J].

Böhm, HJ ;

Banner, D ;

Bendels, S ;

Kansy, M ;

Kuhn, B ;

Müller, K ;

Obst-Sander, U ;

Stahl, M .

CHEMBIOCHEM, 2004, 5 (05) :637-643

[2] Electrosynthesis Using a Recyclable Mediator-Electrolyte System Based on lonically Tagged Phenyl Iodide and 1,1,1,3,3,3-Hexafluoroisopropanol [J].

Broese, Timo ;

Francke, Robert .

ORGANIC LETTERS, 2016, 18 (22) :5896-5899

[3]

Coleman J. P., 1974, J CHEM SOC P2, V9, P1064

[4] Electrochemical Synthesis of Aryl Methoxymethyl Ethers [J].

de Kruijff, Goswinus H. M. ;

Waldvogel, Siegfried R. .

CHEMELECTROCHEM, 2019, 6 (16) :4180-4183

[5] Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron-rich Substrates [J].

Doobary, Sayad ;

Sedikides, Alexi T. ;

Caldora, Henry P. ;

Poole, Darren L. ;

Lennox, Alastair J. J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (03) :1155-1160

[6]

Fäh C, 2010, EUR J ORG CHEM, V2010, P4617, DOI [10.1002/ejoc.201000712, 10.1002/ejoe.201000712]

[7] Selective electrochemical fluorination of organic molecules and macromolecules in ionic liquids [J].

Fuchigami, Toshio ;

Inagi, Shinsuke .

CHEMICAL COMMUNICATIONS, 2011, 47 (37) :10211-10223

[8] The effect of substituents on the anodic oxidation of aliphatic carboxylates and the passage towards a pseudo-Kolbe reaction [J].

Galicia, Monica ;

Gonzalez-Fuentes, Miguel A. ;

Valencia, Drochss P. ;

Gonzalez, Felipe J. .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2012, 672 :28-33

[9] Applications of Fluorine in Medicinal Chemistry [J].

Gillis, Eric P. ;

Eastman, Kyle J. ;

Hill, Matthew D. ;

Donnelly, David J. ;

Meanwell, Nicholas A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (21) :8315-8359

[10] Electrochemical Screening for Electroorganic Synthesis [J].

Guetz, Christoph ;

Kloeckner, Bernhard ;

Waldvogel, Siegfried R. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2016, 20 (01) :26-32

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