Symmetric Aromatic Amidoalkylations of Triphenylenes

• Published in: Chemistry : a European journal Vol. 30; no. 54; pp. e202402348 - n/a
• Main Authors: Lorenzetto, Tommaso, Berton, Giacomo, Castellini, Francesco, Casson, Gabriele, Scarso, Alessandro, Fabris, Fabrizio
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 25.09.2024
• Subjects: Alkylating agents; Alkylation; Amidoalkylation; aromatic substitution; C3-symmetry; C−H alkylation; Triphenylene; triphenylene, amidoalkylation, C3-symmetry, aromatic substitution, C-H alkylation
• ISSN: 0947-6539; 1521-3765; 1521-3765
• DOI: 10.1002/chem.202402348

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. An efficient amidoalkylation method of triphenylene derivatives is reported leading to tris‐alkylated C3‐symmetric compounds in good yields. The reaction takes place in the hindered bay regions of the compound for which very few functionalization methods are known in the literature.