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Acceptorless dehydrogenation of small molecules through cooperative base metal catalysis

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  • Julian G. West

    (Princeton University)

  • David Huang

    (Princeton University)

  • Erik J. Sorensen

    (Princeton University)

Abstract

The dehydrogenation of unactivated alkanes is an important transformation both in industrial and biological systems. Recent efforts towards this reaction have revolved around high temperature, organometallic C–H activation by noble metal catalysts that produce alkenes and hydrogen gas as the sole products. Conversely, natural desaturase systems proceed through stepwise hydrogen atom transfer at physiological temperature; however, these transformations require a terminal oxidant. Here we show combining tetra-n-butylammonium decatungstate (TBADT) and cobaloxime pyridine chloride (COPC) can catalytically dehydrogenate unactivated alkanes and alcohols under near-UV irradiation at room temperature with hydrogen as the sole by-product. This noble metal-free process follows a nature-inspired pathway of high- and low-energy hydrogen atom abstractions. The hydrogen evolution ability of cobaloximes is leveraged to render the system catalytic, with cooperative turnover numbers up to 48 and yields up to 83%. Our results demonstrate how cooperative base metal catalysis can achieve transformations previously restricted to precious metal catalysts.

Suggested Citation

  • Julian G. West & David Huang & Erik J. Sorensen, 2015. "Acceptorless dehydrogenation of small molecules through cooperative base metal catalysis," Nature Communications, Nature, vol. 6(1), pages 1-7, December.
  • Handle: RePEc:nat:natcom:v:6:y:2015:i:1:d:10.1038_ncomms10093
    DOI: 10.1038/ncomms10093
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    Cited by:

    1. Long Huang & Tengfei Ji & Chen Zhu & Huifeng Yue & Nursaya Zhumabay & Magnus Rueping, 2022. "Bioinspired desaturation of alcohols enabled by photoredox proton-coupled electron transfer and cobalt dual catalysis," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Guanghao Ji & Xinqiang Chen & Jing Zhang, 2024. "Direct ketone synthesis from primary alcohols and alkenes enabled by a dual photo/cobalt catalysis," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    3. Jingjing Zhang & Armido Studer, 2022. "Decatungstate-catalyzed radical disulfuration through direct C-H functionalization for the preparation of unsymmetrical disulfides," Nature Communications, Nature, vol. 13(1), pages 1-8, December.

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