Author, as appears in the article.: Carbó, J.J. ; Cuenca, A.B.; Cid, J.; García-López, D.; Fernández, E.

Department: Química Física i Inorgànica

URV's Author/s: CARBÓ MARTIN, JORGE JUAN; Cuenca, A.B.; Cid, J.; García-López, D.; 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

Research group: Química Quàntica Organometàl.lics i Catàlisi Homogènia

Thematic Areas: Chemistry Química Química

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

ISSN: 1477-0520

Author identifier: 0000-0002-3945-6721; 0000-0002-6842-1261; n/a; n/a; 0000-0001-9025-1791

Record's date: 2017-03-17

Last page: 9664

Journal volume: 13

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

Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2015/OB/C5OB01523E#!divAbstract

Article's DOI: 10.1039/c5ob01523e

Entity: Universitat Rovira i Virgili

Journal publication year: 2015

First page: 9659

Publication Type: Article Artículo Article