Synthesis of a Five-Fold-Differentiated 1,3,5,7,9-Pentasubstituted Corannulene: A Maximal Labeling Problem in the Context of Corannulene

Abstract

This work defines a maximally labeled isomer problem in the context of 1,3,5,7,9-pentasubstituted corannulenes and explores two new synthetic strategies for the construction of key C-C bonds in the corannulene nucleus: a) a Diels-Alder cycloaddition of thiophene dioxide and acenaphthene fragments; b) a manganese-mediated reductive coupling of benzylic halides, which tolerates carboxy ester functionality. It advances the area of curved aromatics based on corannulene by setting a new family of targets for chemical synthesis and providing additional general synthetic tools.