Author, as appears in the article.: Cuenca, Ana B.; Cid, Jessica; Garcia-Lopez, Diego; Carbo, Jorge J.; Fernandez, Elena;
Department: Química Física i Inorgànica
URV's Author/s: Carbó Martin, Jorge Juan / Fernández Gutiérrez, Maria Elena
Keywords: Diboron reagents
Abstract: We have experimentally proved the unsymmetrical 1,1-diboration of diazo compounds, formed in situ from aldehydes and cyclic and non-cyclic ketones, in the absence of any transition metal complex. The heterolytic cleavage of the mixed diboron reagent, Bpin-Bdan, and the formation of two geminal C-Bpin and C-Bdan bonds has been rationalised based on DFT calculations to occur via a concerted-asynchronous mechanism. Diastereoselection is attained on substituted cyclohexanones and DFT studies provide understanding on the origin of the selectivity. The alkoxide-assisted selective deborylation of Bpin from the multisubstituted sp3-carbon and generation of a Bdan stabilized carbanion, easily conducts a selective protodeboronation sequence
Thematic Areas: Química Physical and theoretical chemistry Organic chemistry Odontología Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ciências biológicas iii 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/
Author's mail: j.carbo@urv.cat mariaelena.fernandez@urv.cat
Author identifier: 0000-0002-3945-6721 0000-0001-9025-1791
Record's date: 2024-09-07
Papper version: info:eu-repo/semantics/acceptedVersion
Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2015/ob/c5ob01523e
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Organic & Biomolecular Chemistry. 13 (37): 9659-9664
APA: Cuenca, Ana B.; Cid, Jessica; Garcia-Lopez, Diego; Carbo, Jorge J.; Fernandez, Elena; (2015). Unsymmetrical 1,1-diborated multisubstituted sp3-carbons formed via a metal-free concerted-asynchronous mechanism. Organic & Biomolecular Chemistry, 13(37), 9659-9664. DOI: 10.1039/c5ob01523e
Article's DOI: 10.1039/c5ob01523e
Entity: Universitat Rovira i Virgili
Journal publication year: 2015
Publication Type: Journal Publications
Repositori URV