Mononuclear complexes of a tridentate redox-active ligand with sulfonamido groups: Structure, properties, and reactivity

Sarah A. Cook, Justin A. Bogart, Noam Levi, Andrew C. Weitz, Curtis Moore, Arnold L. Rheingold, Joseph W. Ziller, Michael P. Hendrich, A. S. Borovik

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The design of molecular complexes of earth-abundant first-row transition metals that can catalyze multi-electron C-H bond activation processes is of interest for achieving efficient, low-cost syntheses of target molecules. To overcome the propensity of these metals to perform single-electron processes, redox-active ligands have been utilized to provide additional electron equivalents. Herein, we report the synthesis of a novel redox active ligand, [ibaps]3-, which binds to transition metals such as FeII and CoII in a meridional fashion through the three anionic nitrogen atoms and provides additional coordination sites for other ligands. In this study, the neutral bidentate ligand 2,2′-bipyridine (bpy) was used to complete the coordination spheres of the metal ions and form NEt4[MII(ibaps)bpy] (M = Fe (1) or Co (1-Co)) salts. The FeII salt exhibited rich electrochemical properties and could be chemically oxidized by 1 and 2 equiv. of ferrocenium to form singly and doubly oxidized species, respectively. The reactivity of 1 towards intramolecular C-H bond amination of aryl azides at benzylic and aliphatic carbon centers was explored, and moderate to good yields of the resulting indoline products were obtained.

Original languageEnglish
Pages (from-to)6540-6547
Number of pages8
JournalChemical Science
Volume9
Issue number31
DOIs
StatePublished - 21 Aug 2018
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2018 The Royal Society of Chemistry.

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