The use of redox non-innocent ligands in transition metal catalysis has emerged as a promising strategy for facilitating multi-electron reactivity. This strategy allows first row transition metals and base metals to facilitate redox reactivity more traditionally mediated by precious metal complexes. Similarly, ligands with pendant H donors in the form of H+, H-atoms, or H-, have been shown to mediate the movement of H for catalytic processes. While both strategies are effective individually, recent studies have focused on combining redox active ligands with pendant H equivalents to perform multi-electron, multi-proton transformations. In this work, the Fe(II) complex of a reduced di-tert-butyl hydrazonopyrrole (tBuDHP) ligand has been isolated and characterized. This complex has been shown to contain pendant H bonded to the beta N atom of each hydrazone moiety on the ligand. This complex reacts with O2 or under 1 atm of air rapidly at room temperature to form a red final complex, likely via an Fe-oxygen intermediate. Additionally, in the presence of benzoquinone, an equivalent of H2 is removed from the ligand to form hydroquinone. Further studies to confirm the identity of these more oxidized species and investigate their reactivity are currently underway. Additionally, the mechanism of these transformations with the Fe complexes will be explored with a focus towards understanding the role of the redox non-innocent ligand and pendant H donors.

Synthesis and reactivity of iron complexes with a redox active dihydrazonopyrrole ligand

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.