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Selective Ortho-Hydroxylation–Defluorination of 2-Fluorophenolates with a Bis(m-oxo)dicopper(III) Species

Aquest mateix article està publicat a l’edició alemanya d’’Angewandte Chemie’ (ISSN 0044-8249, EISSN 1521-3757), 2014, vol. 126, núm. 36, p. 9762-9766. DOI http://dx.doi.org/10.1002/ange.201405060

The bis(mu-oxo) dicopper(III) species [Cu-III 2(mu-O)(2)(m-XYLMeAN)](2+) (1) promotes the electrophilic ortho-hydroxylation-defluorination of 2-fluorophenolates to give the corresponding catechols, a reaction that is not accomplishable with a (eta(2) : eta(2)-O-2) dicopper(II) complex. Isotopic labeling studies show that the incoming oxygen atom originates from the bis(mu-oxo) unit. Ortho-hydroxylation-defluorination occurs selectively in intramolecular competition with other ortho-substituents such as chlorine or bromine

Financial support for this work was provided by the European Commission (FP7-PEOPLE-2011-CIG-303522 to A. C.; ERC-2009-StG-239910 to M. C., and Marie Curie IOF to I. G.-B.), MINECO (CTQ2012-37420-C02-01/BQU and CSD2010-00065 to M. C.), Generalitat de Catalunya (ICREA Academia Award to M. C.), Spanish Ministry of Science (Ramon y Cajal contract to A. C.), and the INNPLANTA project INP-2011-0059-PCT-420000-ACT1 (Dr. X. Ribas). We also thank Dr. Laura Gomez (Serveis Tecnics de Recerca, Universitat de Girona) for helpful advice in setting up the HR-MS experiments, and for fruitful discussions

info:eu-repo/grantAgreement/MINECO//CTQ2012-37420-C02-01/ES/DISEÑO BIOINSPIRADO DE CATALIZADORES PARA LA OXIDACION DE ENLACES C-H, C=C Y AGUA/

Wiley-VCH Verlag

Manager: Ministerio de Economía y Competitividad (Espanya)
Ministerio de Ciencia e Innovación (Espanya)
Author: Serrano Plana, Joan
Garcia Bosch, Isaac
Miyake, Ryosuke
Costas Salgueiro, Miquel
Company Casadevall, Anna
Abstract: Aquest mateix article està publicat a l’edició alemanya d’’Angewandte Chemie’ (ISSN 0044-8249, EISSN 1521-3757), 2014, vol. 126, núm. 36, p. 9762-9766. DOI http://dx.doi.org/10.1002/ange.201405060
The bis(mu-oxo) dicopper(III) species [Cu-III 2(mu-O)(2)(m-XYLMeAN)](2+) (1) promotes the electrophilic ortho-hydroxylation-defluorination of 2-fluorophenolates to give the corresponding catechols, a reaction that is not accomplishable with a (eta(2) : eta(2)-O-2) dicopper(II) complex. Isotopic labeling studies show that the incoming oxygen atom originates from the bis(mu-oxo) unit. Ortho-hydroxylation-defluorination occurs selectively in intramolecular competition with other ortho-substituents such as chlorine or bromine
Financial support for this work was provided by the European Commission (FP7-PEOPLE-2011-CIG-303522 to A. C.; ERC-2009-StG-239910 to M. C., and Marie Curie IOF to I. G.-B.), MINECO (CTQ2012-37420-C02-01/BQU and CSD2010-00065 to M. C.), Generalitat de Catalunya (ICREA Academia Award to M. C.), Spanish Ministry of Science (Ramon y Cajal contract to A. C.), and the INNPLANTA project INP-2011-0059-PCT-420000-ACT1 (Dr. X. Ribas). We also thank Dr. Laura Gomez (Serveis Tecnics de Recerca, Universitat de Girona) for helpful advice in setting up the HR-MS experiments, and for fruitful discussions
Format: application/pdf
Document access: http://hdl.handle.net/10256/10332
Language: eng
Publisher: Wiley-VCH Verlag
Collection: info:eu-repo/semantics/altIdentifier/doi/10.1002/anie.201405060
info:eu-repo/semantics/altIdentifier/issn/1433-7851
info:eu-repo/semantics/altIdentifier/eissn/1521-3773
MICINN/PN 2010-2016/CSD2010-00065
MICINN/PN 2011/INP-2011-0059-PCT-420000
info:eu-repo/grantAgreement/EC/FP7/303522/EU/Key insights into oxidation chemistry through synthetic systems: N2O activation with first-row transition-metals and O2 activation in heterobimetallic Fe-Ni systems/NEWOXMET
info:eu-repo/grantAgreement/EC/FP7/239910/EU/Bio-inspired Design of Catalysts for Selective Oxidations of C-H and C=C Bonds/BIDECASEOX
Is part of: info:eu-repo/grantAgreement/MINECO//CTQ2012-37420-C02-01/ES/DISEÑO BIOINSPIRADO DE CATALIZADORES PARA LA OXIDACION DE ENLACES C-H, C=C Y AGUA/
Rights: Tots els drets reservats
Subject: Coure -- Compostos
Copper compounds
Title: Selective Ortho-Hydroxylation–Defluorination of 2-Fluorophenolates with a Bis(m-oxo)dicopper(III) Species
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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