Symmetric Aromatic Amidoalkylations of Triphenylenes

Chemistry. 2024 Sep 25;30(54):e202402348. doi: 10.1002/chem.202402348. Epub 2024 Sep 9.

Abstract

Triphenylene derivatives are highly investigated for their electronic, supramolecular and photophysical properties, but the direct modification of the central aromatic core is particularly challenging especially in the internal positions 1, 4, 5, 8, 9, and 12. Herein we present an efficient alkylation method of 2,3,6,7,10,11-hexasubstituted triphenylene derivatives leading to tris-alkylated C3-symmetric derivatives in good yields using N-(hydroxymethyl)carboxamide or N-(alkoxylmethyl)carboxamide alkylating agents.

Keywords: Amidoalkylation; C3-symmetry; C−H alkylation; Triphenylene; aromatic substitution.