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Issue 31, 2018
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Mononuclear complexes of a tridentate redox-active ligand with sulfonamido groups: structure, properties, and reactivity

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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.

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

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Publication details

The article was received on 23 Dec 2017, accepted on 30 Jun 2018 and first published on 02 Jul 2018


Article type: Edge Article
DOI: 10.1039/C7SC05445A
Citation: Chem. Sci., 2018,9, 6540-6547
  • Open access: Creative Commons BY license
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    Mononuclear complexes of a tridentate redox-active ligand with sulfonamido groups: structure, properties, and reactivity

    S. A. Cook, J. A. Bogart, N. Levi, A. C. Weitz, C. Moore, A. L. Rheingold, J. W. Ziller, M. P. Hendrich and A. S. Borovik, Chem. Sci., 2018, 9, 6540
    DOI: 10.1039/C7SC05445A

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