Issue 7, 2023

An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex

Abstract

The extensively studied organic material 5,10,15-triazatruxene is usually synthesized by the trimerization of indole or 2-indolone using the toxic liquid bromine and phosphoryl chloride. Herein, we report an efficient synthetic approach towards 5,10,15-triazatruxene by the condensation of 2-bromoaniline and phloroglucinol followed by palladium-catalyzed intramolecular C–H bond arylation. The regioselective iridium-catalyzed borylation occurred at the 1,6,11-positions of tert-butylated triazatruxene to generate a triboronic ester quantitatively. Pyridine groups were introduced via the Suzuki–Miyaura cross-coupling reaction to afford a precursor of a triazatruxene-based boron difluoride complex with a large Stokes shift.

Graphical abstract: An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex

Supplementary files

Article information

Article type
Research Article
Submitted
31 jan 2023
Accepted
27 fev 2023
First published
28 fev 2023

Org. Chem. Front., 2023,10, 1811-1816

An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex

Y. Wang, S. Chen and G. Zhang, Org. Chem. Front., 2023, 10, 1811 DOI: 10.1039/D3QO00144J

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