On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water

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 t...

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Detalles Bibliográficos
Autores: Martínez López, Juan Pablo, Solà i Puig, Miquel, Poater Teixidor, Albert
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/11791
Acceso en línea:http://hdl.handle.net/10256/11791
Access Level:acceso abierto
Palabra clave:Funcional de densitat, Teoria del
Density functionals
Química verda
Green chemistry
Catàlisi homogènia
Homogeneous catalysis
Rodi
Rhodium
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spelling On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of WaterMartínez López, Juan PabloSolà i Puig, MiquelPoater Teixidor, AlbertFuncional de densitat, Teoria delDensity functionalsQuímica verdaGreen chemistryCatàlisi homogèniaHomogeneous catalysisRodiRhodiumDensity 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 protonsA.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-PWileyMinisterio de Economía y Competitividad (Espanya)Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca2015info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10256/11791http://hdl.handle.net/10256/11791ChemistryOpen, 2015, vol. 4, núm. 6, p. 774-778Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1002/open.201500093info:eu-repo/semantics/altIdentifier/eissn/2191-1363info:eu-repo/grantAgreement/MICINN//RYC-2009-05226info:eu-repo/grantAgreement/MINECO//CTQ2014-59832-JINAGAUR/2014-2016/2014 SGR-931info:eu-repo/grantAgreement/MINECO//CTQ2014-54306-Pinfo:eu-repo/grantAgreement/EC/FP7/293900Attribution-NonCommercial-NoDerivs 3.0 Spainhttp://creativecommons.org/licenses/by-nc-nd/3.0/es/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/117912026-05-29T05:05:01Z
dc.title.none.fl_str_mv On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
title On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
spellingShingle On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
Martínez López, Juan Pablo
Funcional de densitat, Teoria del
Density functionals
Química verda
Green chemistry
Catàlisi homogènia
Homogeneous catalysis
Rodi
Rhodium
title_short On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
title_full On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
title_fullStr On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
title_full_unstemmed On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
title_sort On the Reaction Mechanism of the Rhodium-Catalyzed Arylation of Fullerene (C60) with Organoboron Compounds in the Presence of Water
dc.creator.none.fl_str_mv Martínez López, Juan Pablo
Solà i Puig, Miquel
Poater Teixidor, Albert
author Martínez López, Juan Pablo
author_facet Martínez López, Juan Pablo
Solà i Puig, Miquel
Poater Teixidor, Albert
author_role author
author2 Solà i Puig, Miquel
Poater Teixidor, Albert
author2_role author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (Espanya)
Generalitat de Catalunya. Agència de Gestió d'Ajuts Universitaris i de Recerca
dc.subject.none.fl_str_mv Funcional de densitat, Teoria del
Density functionals
Química verda
Green chemistry
Catàlisi homogènia
Homogeneous catalysis
Rodi
Rhodium
topic Funcional de densitat, Teoria del
Density functionals
Química verda
Green chemistry
Catàlisi homogènia
Homogeneous catalysis
Rodi
Rhodium
description 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
publishDate 2015
dc.date.none.fl_str_mv 2015
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/11791
http://hdl.handle.net/10256/11791
url http://hdl.handle.net/10256/11791
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/open.201500093
info:eu-repo/semantics/altIdentifier/eissn/2191-1363
info:eu-repo/grantAgreement/MICINN//RYC-2009-05226
info:eu-repo/grantAgreement/MINECO//CTQ2014-59832-JIN
AGAUR/2014-2016/2014 SGR-931
info:eu-repo/grantAgreement/MINECO//CTQ2014-54306-P
info:eu-repo/grantAgreement/EC/FP7/293900
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivs 3.0 Spain
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivs 3.0 Spain
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv ChemistryOpen, 2015, vol. 4, núm. 6, p. 774-778
Articles publicats (D-Q)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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