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Mechanistic Insights into Iron-Catalyzed C-H Bond Activation and C-C Coupling. 2021

Samantha M Brewer, and Timothy M Schwartz, and Magy A Mekhail, and Lara S Turan, and Timothy J Prior, and Timothy J Hubin, and Benjamin G Janesko, and Kayla N Green
Department of Chemistry and Biochemistry, Texas Christian University, Fort Worth, Texas 76129, United States.

Iron-catalyzed C-C coupling reactions of pyrrole provide a unique alternative to the traditional Pd-catalyzed counterpart. However, many details regarding the actual mechanism remain unknown. A series of macrocyclic iron(III) complexes were used to evaluate specifics related to the role of O2, radicals, and μ-oxodiiron-complex participation in the catalytic cycle. It was determined that the mononuclear tetra-azamacrocyclic complex is a true catalyst and not a stoichiometric reagent, while more than one equivalent of a sacrificial oxidant is needed. Furthermore, the reaction does not proceed through an organic radical pathway. μ-Oxodiiron complexes are not involved in the main catalytic pathway, and the dimers are, in fact, off-cycle species that decrease catalytic efficiency.

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