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Issue 40, 2019
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Electrochemical C–H bond activation via cationic iridium hydride pincer complexes

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Abstract

A C–H bond activation strategy based on electrochemical activation of a metal hydride is introduced. Electrochemical oxidation of (tBu4PCP)IrH4 (tBu4PCP is [1,3-(tBu2PCH2)-C6H3]) in the presence of pyridine derivatives generates cationic Ir hydride complexes of the type [(tBu4PCP)IrH(L)]+ (where L = pyridine, 2,6-lutidine, or 2-phenylpyridine). Facile deprotonation of [(tBu4PCP)IrH(2,6-lutidine)]+ with the phosphazene base tert-butylimino-tris(pyrrolidino)phosphorane, tBuP1(pyrr), results in selective C–H activation of 1,2-difluorobenzene (1,2-DFB) solvent to generate (tBu4PCP)Ir(H)(2,3-C6F2H3). The overall electrochemical C–H activation reaction proceeds at room temperature without need for chemical activation by a sacrificial alkene hydrogen acceptor. This rare example of undirected electrochemical C–H activation holds promise for the development of future catalytic processes.

Graphical abstract: Electrochemical C–H bond activation via cationic iridium hydride pincer complexes

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Publication details

The article was received on 21 Jun 2019, accepted on 19 Aug 2019 and first published on 20 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03076J
Chem. Sci., 2019,10, 9326-9330
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Electrochemical C–H bond activation via cationic iridium hydride pincer complexes

    B. M. Lindley, A. G. Walden, A. M. Brasacchio, A. Casuras, N. Lease, C. Chen, A. S. Goldman and A. J. M. Miller, Chem. Sci., 2019, 10, 9326
    DOI: 10.1039/C9SC03076J

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