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

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journal contribution
posted on 04.08.2014, 00:00 by Heather L. Buckley, Leah K. Rubin, Mikołaj Chromiński, Brendon J. McNicholas, Katherine H. Y. Tsen, Daniel T. Gryko, John Arnold
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)­corroleH3 (1) and ((C6F5)2(m-CH2N3)­Ph)­corroleH3 (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.