Corroles That €œClick €?: Modular Synthesis of Azido- and Propargyl-Functionalized Metallocorrole Complexes and Convergent Synthesis of a Bis-corrole Scaffold
By Buckley, Heather L.; Rubin, Leah K.; Chromiš„ski, Mikoš‚aj; McNicholas, Brendon J.; Tsen, Katherine H. Y.; Gryko, Daniel T. & Arnold, John
Published in Inorganic Chemistry
2014
Abstract
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.