C−H Functionalization of BN-Aromatics Promoted by Addition of Organolithium Compounds to the Boron Atom
Authors
Abengózar Muñoz, Alberto; Fernández González, Miguel Ángel; Sucunza Sáenz, David; Frutos Gaite, Luis Manuel; Salgado Serrano, Antonio; [et al.]Identifiers
Permanent link (URI): http://hdl.handle.net/10017/43801DOI: 10.1021/acs.orglett.8b02040
ISSN: 1523-7060
Date
2018-08-17Affiliation
Universidad de Alcalá. Departamento de Química Analítica, Química Física e Ingeniería Química; Universidad de Alcalá. Departamento de Química Orgánica y Química InorgánicaBibliographic citation
Organic Letters, 2018, v. 20, n. 16, p. 4902-4906
Keywords
BN-phenanthrene
C-H functionalization
organolithium compound
NMR
DFT
Project
CTQ2014-52488-R, CTQ2016-80600-P, CTQ2017-85263-R (Ministerio de Economía y Competitividad, AEI and FEDER); RETIC REDINREN RD16/0009/0015 (Instituto de Salud Carlos III, FEDER); CCGP2017-EXP012 (University of Alcalá)
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
© 2018 American Chemical Society
Access rights
info:eu-repo/semantics/openAccess
Abstract
Addition of an organolithium compound to a BN-phenanthrene with embedded B and N atoms is proposed to result in coordination of RLi to the boron atom. This coordination, supported by NMR spectroscopy and DFT calculations, increases the nucleophilicity of the system in the b position to the N atom, and is therefore a useful tool for promoting regioselective C-H functionalization of BN aromatics
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