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TITLE:
Borylation of conjugated dienes with diboranes. A stereo- and chemoselective analysis - TFM:1330
Handle: https://hdl.handle.net/20.500.11797/TFM1330

Student:Bru Garcia, Gerard
Language:en
Title in original language:Borylation of conjugated dienes with diboranes. A stereo- and chemoselective analysis
Title in different languages:Borylation of conjugated dienes with diboranes. A stereo- and chemoselective analysis
Keywords:borylation, dienes, DFT
Subject:química
Abstract:The transition metal-free borylation of 1,3-disubstituted conjugated dienes through the in situ formation of adduct [MeO-Bpin-Bpin]-, to promote allylic borylative sequences was explored. For (3-methylbuta-1,3-dien-1-yl)benzene we observed an allylic borylation followed by 1,2 hydroboration. The 1,2-hydroboration locates the Bpin moiety at the more hindered position of the allylborane. Intramolecular Pd catalyzed cross-coupling with borylated products containing Ar-Br functionalities, favoured chemoselective intramolecular cross-coupling reaction, generating tetrahydronaphthalenes. With DFT studies we have characterized the mechanism for the borylation reaction and rationalized the observed stereoselectivity. We explored state-of-the-art computational methodologies to analyze post-transition state bifurcations and rationalize the observed borylative pathways.
Project director:Carbó Martin, Jorge Juan; Fernández Gutiérrez, Maria Elena
Department:Química Física i Inorgànica
Education area(s):Síntesi, Catàlisi i Disseny Molecular
Entity:Universitat Rovira i Virgili (URV)
Work's public defense date:2022-07-25
Academic year:2021-2022
Confidenciality:No
Subject areas:Chemistry
APS:NO
Creation date in repository:2023-05-22
Access Rights:info:eu-repo/semantics/openAccess
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