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Base-Promoted C–O Bond Cleavage of Primary Alcohols by Iridium(III) Porphyrin Chloride

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Organometallics 2020, 39, 8, 1376-1383
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    Base-Promoted C–O Bond Cleavage of Primary Alcohols by Iridium(III) Porphyrin Chloride
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    • Yongjun Bian
      Yongjun Bian
      College of Chemistry and Chemical Engineering, Jinzhong University, Yuci 030619, People’s Republic of China
      Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, People’s Republic of China
      More by Yongjun Bian
      Orcidhttp://orcid.org/0000-0001-9433-974X
    • Xingyu Qu
      Xingyu Qu
      College of Chemistry and Chemical Engineering, Jinzhong University, Yuci 030619, People’s Republic of China
      Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, People’s Republic of China
      More by Xingyu Qu
    • Kin Shing Chan*
      Kin Shing Chan
      Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, People’s Republic of China
      School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210046, People’s Republic of China
      *E-mail for K.S.C.: [email protected]
      More by Kin Shing Chan
      Orcidhttp://orcid.org/0000-0002-1112-6819
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    Organometallics

    Cite this: Organometallics 2020, 39, 8, 1376–1383
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    https://doi.org/10.1021/acs.organomet.0c00100
    Published April 3, 2020
    Copyright © 2020 American Chemical Society
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    Abstract

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    Various Ir(por)-benzyls and Ir(por)-alkyls (por = porphyrinato dianion ligand) were successfully synthesized with benzyl and 1° alkyl alcohols by C–O bond cleavage with Ir(ttp)(CO)Cl (ttp = 5,10,15,20-tetraphenylporphyrinato dianion) in alkaline media. The alkylation products were afforded in up to 92% yields. Mechanistic investigations suggest that both the Ir(ttp)− anion and Ir(ttp)H are key intermediates via a hydrogen-borrowing pathway.

    Copyright © 2020 American Chemical Society

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    This article is cited by 3 publications.

    1. E. Yu. Tyulyaeva. Noble Metal Porphyrin Complexes. Intermediates of Catalytic Processes (A Review). Russian Journal of Inorganic Chemistry 2023, 68 (11) , 1537-1561. https://doi.org/10.1134/S0036023623602143
    2. E. Yu. Tyulyaeva. Noble Metal Porphyrin Complexes. Intermediates of Catalytic Processes (A Review). Журнал неорганической химии 2023, 68 (11) , 1552-1577. https://doi.org/10.31857/S0044457X23600330
    3. E. Yu. Tyulyaeva, N. G. Bichan, T. N. Lomova. Generation and Spectral Properties of Oxidized Forms of Iridium and Rhenium Porphyrin Complexes. Russian Journal of Inorganic Chemistry 2022, 67 (3) , 338-349. https://doi.org/10.1134/S0036023622030147
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    Organometallics

    Cite this: Organometallics 2020, 39, 8, 1376–1383
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.organomet.0c00100
    Published April 3, 2020
    Copyright © 2020 American Chemical Society
    Request reuse permissions

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