An alternative approach to triazatruxene synthesis and derivatization to a boron difluoride complex. Issue 7 (8th March 2023)

• Record Type: Journal Article
• Authors: Wang, Yuheng; Chen, Si; Zhang, Gang
• Is Part Of: Organic chemistry frontiers. Volume 10:Issue 7(2023)
• Page Start: 1811
• Page End: 1816
• Publication Date: 2023-03-08
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d3qo00144j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An alternative method to access 5, 10, 15-triazatruxene has been developed. The 1, 6, 11-positions of triazatruxene can further be functionalized to construct a boron difluoride complex with a large Stokes shift. 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.