β-Functionalization of 4a-aza-8a-boranaphthalene via Iridium-catalyzed C-H Borylation
Authors
Valencia Nieto, Isabel; Sucunza Sáenz, David; Mendicuti Madrid, Francisco Enrique Javier; García García, Patricia; Vaquero López, Juan JoséIdentifiers
Permanent link (URI): http://hdl.handle.net/10017/59187DOI: 10.1002/adsc.202300408
ISSN: 1615-4150
Date
2023-07-02Affiliation
Universidad de Alcalá. Departamento de Química Analítica, Química Física e Ingeniería Química; Universidad de Alcalá. Departamento de Química Orgánica y Química InorgánicaFunders
Ministerio de Ciencia e Innovación
Instituto de Salud Carlos III
Bibliographic citation
Advanced Synthesis and Catalysis, 2023, v. 365, n. 15, p. 2545-2552
Keywords
BN-naphthalene
C-H activation
iridiumcross-coupling
catalysis
Project
info:eu-repo/grantAgreement/MICINN//PID2020-115128RB-I00/ES/
info:eu-repo/grantAgreement/MICINN//PID2021-1242470B-C21/ES/
info:eu-repo/grantAgreement/MICINN//PID2020-118384GB-I00/ES/
info:eu-repo/grantAgreement/ISCIII//ISCIIIRICORS2040%2FRD21%2F0005%2F0005/ES/
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
© The Authors
Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
Access rights
info:eu-repo/semantics/openAccess
Abstract
A general method for the functionalization of 4a-aza-8a-boranaphthalene in the position ? to the nitrogen atom has been developed. This method is based on a regioselective iridium-catalyzed C?H activation process for the introduction of a boronate group, which can subsequently be transformed into a variety of aryl or alkynyl groups via cross-coupling reactions. Selective mono- or difunctionalization can be achieved by controlling the reaction conditions during the borylation step. The photophysical properties of the obtained 3- or 3,6-substituted BN-naphthalenes have been evaluated, and some of them have been found to be significantly fluorescent, with fluorescence quantum yields up to 0.85.
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Beta_Valencia_AdvSynthCat_2023.pdf | 6.068Mb |
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Beta_Valencia_AdvSynthCat_2023.pdf | 6.068Mb |
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