Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction

dc.creatorBraga, AAC
dc.creatorMorgon, NH
dc.creatorUjaque, G
dc.creatorMaseras, F
dc.date2005
dc.date47270
dc.date2014-11-17T11:14:35Z
dc.date2015-11-26T16:42:27Z
dc.date2014-11-17T11:14:35Z
dc.date2015-11-26T16:42:27Z
dc.date.accessioned2018-03-28T23:27:02Z
dc.date.available2018-03-28T23:27:02Z
dc.identifierJournal Of The American Chemical Society. Amer Chemical Soc, v. 127, n. 25, n. 9298, n. 9307, 2005.
dc.identifier0002-7863
dc.identifierWOS:000230010600076
dc.identifier10.1021/ja050583l
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/56407
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/56407
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/56407
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1273262
dc.descriptionThe role of the base in the transmetalation step of the Suzuki-Miyaura cross-coupling reaction is analyzed computationally by means of DFT calculations with the Becke3LYP functional. The model system studied consists of Pd(CH=CH(2))(PH(3))(2)Br as the starting catalyst complex, CH(2)=CHB(OH)(2) as the organoboronic acid, and OH(-) as the base. The two main mechanistic proposals, consisting of the base attacking first either the palladium complex or the organoboronic acid, are evaluated through geometry optimization of the corresponding intermediates and transition states. Supplementary calculations are carried out on the uncatalyzed reaction and on a process where the starting complex is Pd(CH=CH(2))(PH(3))(2)(OH). These calculations, considered together with available experimental data, strongly suggest that the main mechanism of transmetalation in the catalytic cycle starts with the reaction of the base and the organoboronic acid.
dc.description127
dc.description25
dc.description9298
dc.description9307
dc.languageen
dc.publisherAmer Chemical Soc
dc.publisherWashington
dc.publisherEUA
dc.relationJournal Of The American Chemical Society
dc.relationJ. Am. Chem. Soc.
dc.rightsfechado
dc.sourceWeb of Science
dc.subjectMolecular-orbital Methods
dc.subjectOrganoboron Compounds
dc.subjectAryl Chlorides
dc.subjectPalladium(0) Complexes
dc.subjectOxidative Addition
dc.subjectHeck Reaction
dc.subjectArylboronic Acids
dc.subjectStille Reaction
dc.subjectBasis-sets
dc.subjectC-c
dc.titleComputational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction
dc.typeArtículos de revistas


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