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

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          Abstract

          Electrochemical C–H activation proceeds at room temperature upon oxidation of a pincer-ligated iridium complex in the presence of base.

          Abstract

          A C–H bond activation strategy based on electrochemical activation of a metal hydride is introduced. Electrochemical oxidation of ( tBu 4 PCP)IrH 4 ( tBu 4 PCP is [1,3-( t Bu 2PCH 2)-C 6H 3] ) in the presence of pyridine derivatives generates cationic Ir hydride complexes of the type [( tBu 4 PCP)IrH(L)] + (where L = pyridine, 2,6-lutidine, or 2-phenylpyridine). Facile deprotonation of [( tBu 4 PCP)IrH(2,6-lutidine)] + with the phosphazene base tert-butylimino-tris(pyrrolidino)phosphorane, t BuP 1(pyrr), results in selective C–H activation of 1,2-difluorobenzene (1,2-DFB) solvent to generate ( tBu 4 PCP)Ir(H)(2,3-C 6F 2H 3). 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.

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          Author and article information

          Journal
          Chem Sci
          Chem Sci
          Chemical Science
          Royal Society of Chemistry
          2041-6520
          2041-6539
          20 August 2019
          28 October 2019
          20 August 2019
          : 10
          : 40
          : 9326-9330
          Affiliations
          [a ] Department of Chemistry , University of North Carolina at Chapel Hill , Chapel Hill , North Carolina 27599-3290 , USA . Email: ajmm@ 123456email.unc.edu
          [b ] Oglethorpe University , Atlanta , Georgia 30319 , USA
          [c ] High Point University , High Point , NC 27262 , USA
          [d ] Rutgers, The State University of New Jersey , New Brunswick , New Jersey 08903 , USA
          Author notes

          ‡These co-authors contributed equally.

          Article
          c9sc03076j
          10.1039/c9sc03076j
          7017868
          This journal is © The Royal Society of Chemistry 2019

          This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)

          Categories
          Chemistry

          Notes

          †Electronic supplementary information (ESI) available. CCDC 1935784, 1935785 and 1935786. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9sc03076j

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