Author, as appears in the article.: Maza RJ, Davenport E, Miralles N, Carbó JJ, Fernández E

Department: Química Física i Inorgànica

URV's Author/s: Carbó Martin, Jorge Juan / Fernández Gutiérrez, Maria Elena / MIRALLES PRAT, NURIA

Keywords: Hydroboration Diboration Conjugated dienes Catalyzed 1,4-hydroboration Aldehydes 1,4-diboration

Abstract: This work explains the reactivity of diboron reagents with 1,3-dienes in a transition-metal-free context. The sole addition of Na2CO3 (30 mol %) to bis(pinacolato)diboron in MeOH allows the 1,4-hydroboration of cyclic and noncyclic 1,3-dienes. The electronic influence on the substrate guarantees the conjugated 1,4-hydroboration versus 1,2-diboration. DFT calculations show that the distribution of charge in the allylic anion intermediate governs the selectivity toward 1,4-hydroboration, while the favored trans configuration in diene reagents determines the preference for the E allyl boronate products.

Thematic Areas: Química Physical and theoretical chemistry Organic chemistry Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, organic Biotecnología Biodiversidade Biochemistry

licence for use: https://creativecommons.org/licenses/by/3.0/es/

ISSN: 15237060

Author's mail: mariaelena.fernandez@urv.cat j.carbo@urv.cat

Author identifier: 0000-0001-9025-1791 0000-0002-3945-6721

Record's date: 2023-02-26

Papper version: info:eu-repo/semantics/acceptedVersion

Link to the original source: https://pubs.acs.org/doi/10.1021/acs.orglett.9b00531

Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/

Papper original source: Organic Letters. 21 (7): 2251-2255

APA: Maza RJ, Davenport E, Miralles N, Carbó JJ, Fernández E (2019). Transition-Metal-Free Allylic Borylation of 1,3-Dienes. Organic Letters, 21(7), 2251-2255. DOI: 10.1021/acs.orglett.9b00531

Article's DOI: 10.1021/acs.orglett.9b00531

Entity: Universitat Rovira i Virgili

Journal publication year: 2019

Publication Type: Journal Publications