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Updated: Sep 10, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Modular α-Functionalization of Bowl-Shaped Subphthalocyanine Aromatics
Jorge Labrador-Santiago1, Marta Gómez-Gómez1, Juan Laforga-Martín1
1Department of Organic Chemistry, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain.
None:
Herein a general strategy for the α-functionalization of subphthalocyanines (SubPcs) via palladium-catalyzed cross-coupling reactions is described. Despite the higher steric demand of α-SubPcs, C3-symmetric iodinated precursors were found to readily undergo α-arylation, alkynylation, alkenylation, and C-N coupling. This strategy is also applicable to enantiopure and even more sterically congested (C1-symmetric) tri- and hexa-substituted derivatives. Thus, these results open the door to a previously inaccessible regioisomeric target for the design of functional nonplanar aromatics.
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