Corroles That Click: Modular Synthesis of Azido- and Propargyl-Functionalized Metallocorrole Complexes and Convergent Synthesis of a Bis-corrole Scaffold

Bis-corroles have been prepared through a convergent synthesis using a copper-catalyzed azide-alkyne cycloaddition. Synthesis of the final homo- and heterobimetallic complexes has been achieved in three to four steps from commercially available materials in good overall yield. Meso-substituted corroles functionalized with a single azido or propargyl group were used as key starting materials. (C6F5)(2)(p-O(CH2CCH)Ph)corroleH(3) (I) and ((C6F5)2(m-CH2N3)Ph)corroleH(3) (3) were metalated with copper or iron and attached by Huisgen azide-alkyne cycloaddition (click reaction) first to small substrates and then to each other, demonstrating a convergent synthesis of bimetallic bis-corrole molecules.