Borylation of conjugated dienes with diboranes. A stereo- and chemoselective analysis

Entity: Universitat Rovira i Virgili (URV)

Confidenciality: No

Education area(s): Síntesi, Catàlisi i Disseny Molecular

APS: NO

Title in different languages: Borylation of conjugated dienes with diboranes. A stereo- and chemoselective analysis

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.

Subject: química

Academic year: 2021-2022

Language: en

Work's public defense date: 2022-07-25

Subject areas: Chemistry

Student: Bru Garcia, Gerard

Department: Química Física i Inorgànica

Creation date in repository: 2023-05-22

Keywords: borylation, dienes, DFT

Title in original language: Borylation of conjugated dienes with diboranes. A stereo- and chemoselective analysis

Access Rights: info:eu-repo/semantics/openAccess

Project director: Carbó Martin, Jorge Juan; Fernández Gutiérrez, Maria Elena