Versatile Palladium‐catalyzed intramolecular cyclization to access new luminescent azaphosphaphenalene motifs

Author:

Simoens Andreas1,Kaczmarek Anna M.2,Machado Ian P.2,Van Hecke Kristof3,Stevens Christian V.1ORCID

Affiliation:

1. Department of Green Chemistry and Technology Synthesis Bioresources and Bioorganic Chemistry Research Group Ghent University Coupure Links 653 9000 Ghent Belgium

2. NanoSensing Group Department of Chemistry Ghent University Krijgslaan 281, S3 9000 Ghent Belgium

3. XStruct Department of Chemistry Ghent University Krijgslaan 281, S3 9000 Ghent Belgium

Abstract

AbstractUsing a straightforward sequence of diphosphonylation and a Pd‐catalysed concerted‐metalation‐deprotonation (CMD), a synthetic strategy towards polyaromatic phosphorus containing heterocycles was developed. Herein, we report the synthesis and characterization of new azaphosphaphenalenes, using easily accessible palladium catalysts and starting materials. The key tetrahydroquinoline intermediates of the reaction were synthesised via a fast and effective procedure and could be isolated as such, or further reacted towards the target polyaromatic structures. The obtained products showed interesting luminescent properties and their emission, excitation and quantum yields were evaluated.

Funder

Fonds Wetenschappelijk Onderzoek

Publisher

Wiley

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