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Iron Catalyzed Hydroformylation of Alkenes under Mild Conditions: Evidence of an Fe(II) Catalyzed Process | Journal of the American Chemical Society
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    Iron Catalyzed Hydroformylation of Alkenes under Mild Conditions: Evidence of an Fe(II) Catalyzed Process
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    • Swechchha Pandey
      Swechchha Pandey
      Polymer Science and Engineering Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
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    • K. Vipin Raj
      K. Vipin Raj
      Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
      More by K. Vipin Raj
      Orcidhttp://orcid.org/0000-0002-7178-264X
    • Dinesh R. Shinde
      Dinesh R. Shinde
      Central NMR Facility, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
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    • Kumar Vanka
      Kumar Vanka
      Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
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      Orcidhttp://orcid.org/0000-0001-7301-7573
    • Varchaswal Kashyap
      Varchaswal Kashyap
      Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
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    • Sreekumar Kurungot
      Sreekumar Kurungot
      Physical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
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      Orcidhttp://orcid.org/0000-0001-5446-7923
    • C. P. Vinod
      C. P. Vinod
      Catalysis Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
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      Orcidhttp://orcid.org/0000-0001-9857-4907
    • Samir H. Chikkali*
      Samir H. Chikkali
      Polymer Science and Engineering Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India
      Academy of Scientific and Innovative Research (AcSIR), Anusandhan Bhawan, 2 Rafi Marg, New Delhi-110001, India
      *[email protected]
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      Orcidhttp://orcid.org/0000-0002-8442-1480
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2018, 140, 12, 4430–4439
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    https://doi.org/10.1021/jacs.8b01286
    Published March 11, 2018
    Copyright © 2018 American Chemical Society
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    Earth abundant, first row transition metals offer a cheap and sustainable alternative to the rare and precious metals. However, utilization of first row metals in catalysis requires harsh reaction conditions, suffers from limited activity, and fails to tolerate functional groups. Reported here is a highly efficient iron catalyzed hydroformylation of alkenes under mild conditions. This protocol operates at 10–30 bar syngas pressure below 100 °C, utilizes readily available ligands, and applies to an array of olefins. Thus, the iron precursor [HFe(CO)4]−[Ph3PNPPh3]+ (1) in the presence of triphenyl phosphine catalyzes the hydroformylation of 1-hexene (S2), 1-octene (S1), 1-decene (S3), 1-dodecene (S4), 1-octadecene (S5), trimethoxy(vinyl)silane (S6), trimethyl(vinyl)silane (S7), cardanol (S8), 2,3-dihydrofuran (S9), allyl malonic acid (S10), styrene (S11), 4-methylstyrene (S12), 4-iBu-styrene (S13), 4-tBu-styrene (S14), 4-methoxy styrene (S15), 4-acetoxy styrene (S16), 4-bromo styrene (S17), 4-chloro styrene (S18), 4-vinylbenzonitrile (S19), 4-vinylbenzoic acid (S20), and allyl benzene (S21) to corresponding aldehydes in good to excellent yields. Both electron donating and electron withdrawing substituents could be tolerated and excellent conversions were obtained for S11–S20. Remarkably, the addition of 1 mol % acetic acid promotes the reaction to completion within 16–24 h. Detailed mechanistic investigations revealed in situ formation of an iron-dihydride complex [H2Fe(CO)2(PPh3)2] (A) as an active catalytic species. This finding was further supported by cyclic voltammetry investigations and intermediacy of an Fe(0)–Fe(II) species was established. Combined experimental and computational investigations support the existence of an iron-dihydride as the catalyst resting state, which then follows a Fe(II) based catalytic cycle to produce aldehyde.

    Copyright © 2018 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.8b01286.

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    This article is cited by 52 publications.

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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2018, 140, 12, 4430–4439
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.8b01286
    Published March 11, 2018
    Copyright © 2018 American Chemical Society
    Request reuse permissions

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