β‐Functionalization of 4 a‐aza‐8 a‐boranaphthalene via Iridium‐catalyzed C−H Borylation

Author:

Valencia Isabel1,Sucunza David1,Mendicuti Francisco2,García‐García Patricia1ORCID,Vaquero Juan J.1ORCID

Affiliation:

1. Departamento de Química Orgánica y Química Inorgánica Instituto de Investigación Química “Andrés M. del Río” (IQAR). Universidad de Alcalá (IRYCIS) 28805 Alcalá de Henares Spain

2. Departamento de Química Analítica Química Física e Ingeniería Química, Instituto de Investigación Química “Andrés M. del Río” (IQAR). Universidad de Alcalá 28805 Alcalá de Henares Spain

Abstract

AbstractA general method for the functionalization of 4aaza‐8aboranaphthalene in the position β 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.

Funder

Florida Polytechnic University

Instituto de Salud Carlos III

Publisher

Wiley

Subject

General Chemistry

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