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Metal-free borylation of heteroarenes using ambiphilic aminoboranes : on the importance of sterics in frustrated lewis pair C-H bond activation

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bul.description.provenanceeb spbfr
bul.rights.dateAccepPubl2017-10-18fr
bul.rights.periodeEmbargoP1Yfr
bul.rights.typeDatedatePublicationfr
dc.contributor.authorLégaré-Lavergne, Julien
dc.contributor.authorFontaine, Frédéric-Georges
dc.contributor.authorMisal Castro, Luis Carlos
dc.contributor.authorRochette, Étienne
dc.contributor.authorJayaraman, Arumugam
dc.date.accessioned2018-06-22T13:28:42Z
dc.date.available2018-10-18T00:00:00Z
dc.date.issued2017-10-18
dc.description.abstractTwo novel frustrated Lewis pair (FLP) aminoboranes, (1-Pip-2-BH2-C6H4)2 (2; Pip = piperidyl) and (1-NEt2-2-BH2-C6H4)2 (3; NEt2 = diethylamino), were synthesized, and their structural features were elucidated both in solution and in the solid state. The reactivity of these species for the borylation of heteroarenes was investigated and compared to previously reported (1-TMP-2-BH2-C6H4)2 (1; TMP = tetramethylpiperidyl) and (1-NMe2-2-BH2-C6H4)2 (4; NMe2 = dimethylamino). It was shown that 2 and 3 are more active catalysts for the borylation of heteroarenes than the bulkier analogue 1. Kinetic studies and density functional theory calculations were performed with 1 and 2 to ascertain the influence of the amino group of this FLP-catalyzed transformation. The C–H activation step was found to be more facile with smaller amines at the expense of a more difficult dissociation of the dimeric species. The bench-stable fluoroborate salts of all catalysts (1F–4F) have been synthesized and tested for the borylation reaction. The new precatalysts 2F and 3F are showing higher reaction rates and yields for multigram-scale syntheses.fr
dc.identifier.doi10.1021/jacs.7b08143fr
dc.identifier.issn1520-5126fr
dc.identifier.pubmed28901757fr
dc.identifier.urihttp://hdl.handle.net/20.500.11794/30144
dc.languageengfr
dc.publisherAmerican Chemical Societyfr
dc.rightshttp://purl.org/coar/access_right/c_abf2
dc.subjectPaire d'électrons de Lewisfr
dc.subject.rvmComposés aromatiquesfr
dc.subject.rvmMolécules ambiphilesfr
dc.subject.rvmBoranes -- Dérivésfr
dc.subject.rvmCatalysefr
dc.subject.rvmCarbonefr
dc.subject.rvmHydrogènefr
dc.subject.rvmActivation (Chimie)fr
dc.titleMetal-free borylation of heteroarenes using ambiphilic aminoboranes : on the importance of sterics in frustrated lewis pair C-H bond activationfr
dc.typearticle de recherche
dc.type.legacyCOAR1_1::Texte::Périodique::Revue::Contribution à un journal::Article::Article de recherchefr
dcterms.bibliographicCitationJournal of the American Chemical Society, Vol. 139 (41), 14714-14723 (2017)fr
dspace.accessstatus.time2023-03-26 18:02:20
dspace.entity.typePublication
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rioxxterms.project.funder-nameNatural Sciences and Engineering Research Council of Canadafr
rioxxterms.project.funder-nameCentre de recherche en catalyse et chimie verte (CCCV)fr
rioxxterms.versionAMfr
rioxxterms.version-of-recordhttps://doi.org/10.1021/jacs.7b08143fr
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