On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
dc.contributor.author
dc.date.accessioned
2015-12-21T07:47:14Z
dc.date.available
2015-12-21T07:47:14Z
dc.date.issued
2015
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dc.description.abstract
Density functional theory (DFT) calculations were carried out to study the reaction mechanism of the Suzuki–Miyaura rhodium-catalyzed hydroarylation of fullerene (C60) by phenylboronic acid in the presence of water. As found experimentally, our results confirm that addition of the phenyl group and the hydrogen atom in C60 occurs at the [6,6] bond. The rate-determining step corresponds to the simultaneous transfer of a hydrogen atom from a water molecule to C60 and the recovery of the active species. The use of 2-phenyl-1,3,2-dioxaborinane and the 4,4,5,5-tetramethyl-2-phenyl-1,3,2,-dioxaborolane instead of phenylboronic acid as organoborate agents does not lead to great modifications of the energy profile. The possible higher steric hindrance of 4,4,5,5-tetramethyl-2-phenyl-1,3,2,-dioxaborolane should not inhibit its use in the hydroarylation of C60. Overall, we show how organoboron species arylate C60 in rhodium-based catalysis assisted by water as a source of protons
dc.description.sponsorship
A.P. thanks the Spanish Ministry of Economy and Competitiveness (MINECO) for a Ramûn y Cajal contract (RYC-2009-05226) and grant no. CTQ2014-59832-JIN, and a European Commission Career Integration Grant (CIG09-GA-2011-293900). J.P.M. gratefully acknowledges a Ph.D. fellowship (register/application no. 217067/312543) from the Mexican National Council of Science and Technology (CONACYT). M.S. acknowledges funding through a European Union (EU) FEDER fund (UNGI08-4E-003 and UNGI10-4E-801), the Generalitat de Catalunya (Spain) (project 2014SGR931), a Catalan Institution for Research and Advanced Studies (ICREA) Academia prize (2014), and MINECO project CTQ2014-54306-P
dc.format.mimetype
application/pdf
dc.language.iso
eng
dc.publisher
Wiley
dc.relation
info:eu-repo/grantAgreement/MICINN//RYC-2009-05226/ES/RYC-2009-05226/
info:eu-repo/grantAgreement/MINECO//CTQ2014-59832-JIN/ES/ESCANEO COMPUTACIONAL DE RELACIONES ESTRUCTURA%2FACTIVIDAD DE CATALIZADORES DE OXIDACION DEL AGUA PARA LA GENERACION DE H2/
AGAUR/2014-2016/2014 SGR-931
info:eu-repo/grantAgreement/MINECO//CTQ2014-54306-P/ES/ESTUDIOS TEORICO-EXPERIMENTALES DE CICLACIONES CATALIZADAS POR METALES DE TRANSICION. NUEVOS DESARROLLOS EN AROMATICIDAD, FUNCIONALES DE LA DENSIDAD Y QUIMICA SUPRAMOLECULAR/
dc.relation.isformatof
Reproducció digital del document publicat a: http://dx.doi.org/10.1002/open.201500093
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ChemistryOpen, 2015, vol. 4, núm. 6, p. 774-778
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Articles publicats (D-Q)
dc.rights
Attribution-NonCommercial-NoDerivs 3.0 Spain
dc.rights.uri
dc.subject
dc.title
On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.embargo.terms
Cap
dc.relation.projectID
info:eu-repo/grantAgreement/EC/FP7/293900/EU/Ab initio Statics and Molecular Dynamics Simulation of Olefin Metathesis Catalysts for pharmacological purposes/COMPUTEDRUG
dc.type.version
info:eu-repo/semantics/publishedVersion
dc.identifier.doi
dc.identifier.idgrec
024357
dc.contributor.funder
dc.relation.FundingProgramme
dc.relation.ProjectAcronym
dc.identifier.eissn
2191-1363