Electrochemical O-trifluoromethylation of electron-deficient phenols

A simple and sustainable one-step strategy for the preparation of electron-deficient aryl trifluoromethyl ethers (ArOCF3) from the corresponding phenols by electrochemical synthesis is presented. Anodic oxidation of trifluoromethane sulfinate (Langlois reagent) leads to direct O-trifluoromethylation...

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Autores principales:	Johannes Bernd, Philipp Werner, Marc Zeplichal, Andreas Terfort
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2021
Materias:	Organic electrochemistry Anodic oxidation Trifluoromethylation Phenols Langlois reagent Green chemistry Industrial electrochemistry TP250-261 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/1c97cf7bc0494d34896ded7ea79e0015
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spelling	oai:doaj.org-article:1c97cf7bc0494d34896ded7ea79e00152021-12-02T04:59:57ZElectrochemical O-trifluoromethylation of electron-deficient phenols1388-248110.1016/j.elecom.2021.107165https://doaj.org/article/1c97cf7bc0494d34896ded7ea79e00152021-12-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S1388248121002496https://doaj.org/toc/1388-2481A simple and sustainable one-step strategy for the preparation of electron-deficient aryl trifluoromethyl ethers (ArOCF3) from the corresponding phenols by electrochemical synthesis is presented. Anodic oxidation of trifluoromethane sulfinate (Langlois reagent) leads to direct O-trifluoromethylation of phenol-derivatives bearing fluorine, chlorine, bromine and nitrile substituents under mild conditions in yields up to 75% and in gram-scale. This electrochemical protocol provides an economic and green synthesis for an otherwise inaccessible class of molecules without the need for expensive or toxic reagents, oxidants or metal catalysts.Johannes BerndPhilipp WernerMarc ZeplichalAndreas TerfortElsevierarticleOrganic electrochemistryAnodic oxidationTrifluoromethylationPhenolsLanglois reagentGreen chemistryIndustrial electrochemistryTP250-261ChemistryQD1-999ENElectrochemistry Communications, Vol 133, Iss , Pp 107165- (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Organic electrochemistry Anodic oxidation Trifluoromethylation Phenols Langlois reagent Green chemistry Industrial electrochemistry TP250-261 Chemistry QD1-999
spellingShingle	Organic electrochemistry Anodic oxidation Trifluoromethylation Phenols Langlois reagent Green chemistry Industrial electrochemistry TP250-261 Chemistry QD1-999 Johannes Bernd Philipp Werner Marc Zeplichal Andreas Terfort Electrochemical O-trifluoromethylation of electron-deficient phenols
description	A simple and sustainable one-step strategy for the preparation of electron-deficient aryl trifluoromethyl ethers (ArOCF3) from the corresponding phenols by electrochemical synthesis is presented. Anodic oxidation of trifluoromethane sulfinate (Langlois reagent) leads to direct O-trifluoromethylation of phenol-derivatives bearing fluorine, chlorine, bromine and nitrile substituents under mild conditions in yields up to 75% and in gram-scale. This electrochemical protocol provides an economic and green synthesis for an otherwise inaccessible class of molecules without the need for expensive or toxic reagents, oxidants or metal catalysts.
format	article
author	Johannes Bernd Philipp Werner Marc Zeplichal Andreas Terfort
author_facet	Johannes Bernd Philipp Werner Marc Zeplichal Andreas Terfort
author_sort	Johannes Bernd
title	Electrochemical O-trifluoromethylation of electron-deficient phenols
title_short	Electrochemical O-trifluoromethylation of electron-deficient phenols
title_full	Electrochemical O-trifluoromethylation of electron-deficient phenols
title_fullStr	Electrochemical O-trifluoromethylation of electron-deficient phenols
title_full_unstemmed	Electrochemical O-trifluoromethylation of electron-deficient phenols
title_sort	electrochemical o-trifluoromethylation of electron-deficient phenols
publisher	Elsevier
publishDate	2021
url	https://doaj.org/article/1c97cf7bc0494d34896ded7ea79e0015
work_keys_str_mv	AT johannesbernd electrochemicalotrifluoromethylationofelectrondeficientphenols AT philippwerner electrochemicalotrifluoromethylationofelectrondeficientphenols AT marczeplichal electrochemicalotrifluoromethylationofelectrondeficientphenols AT andreasterfort electrochemicalotrifluoromethylationofelectrondeficientphenols
_version_	1718400877045219328

Electrochemical O-trifluoromethylation of electron-deficient phenols

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