Catalyst-Controlled Regiodivergent C–H Arylation Site of Fluorinated 2‑Arylpyridine Derivatives: Application to Luminescent Iridium(III) Complexes

Regiodivergent C–H bond arylation of fluorinated 2-arylpyridines and 2-arylquinolines has been developed. The use of Pd catalyst allows functionalization of the C–H bond of the aryl flanked by two fluorine atoms (most acidic position), while using Ru catalyst, the arylation takes place on the aryl u...

Full description

Saved in:
Bibliographic Details
Published inACS catalysis Vol. 9; no. 2; pp. 1320 - 1328
Main Authors Boyaala, Rabab, Touzani, Rachid, Roisnel, Thierry, Dorcet, Vincent, Caytan, Elsa, Jacquemin, Denis, Boixel, Julien, Guerchais, Véronique, Doucet, Henri, Soulé, Jean-François
Format Journal Article
LanguageEnglish
Published American Chemical Society 01.02.2019
Subjects
Catalysis
Chemical Sciences
Coordination chemistry
Organic chemistry
iridium
ruthenium
palladium
luminescence
C−H bond functionalization
TD-DFT
C-H bond functionalization
Online AccessGet full text

Cover

More Information
Summary:Regiodivergent C–H bond arylation of fluorinated 2-arylpyridines and 2-arylquinolines has been developed. The use of Pd catalyst allows functionalization of the C–H bond of the aryl flanked by two fluorine atoms (most acidic position), while using Ru catalyst, the arylation takes place on the aryl unit at the ortho position of the heterocycle. Both reaction conditions exhibit a good functional group tolerance. The synthetically useful selectivity observed with Pd catalyst was applied to design C^N ligands for the preparation of luminescent cationic iridium­(III) complexes. The influence of the incorporated aryl group onto the fluorinated phenyl unit and the fluorine position patterns on the photophysical properties is described.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.8b04553