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Facile scission of isonitrile carbon–nitrogen triple bond using a diborane(4) reagent

Author

Listed:
  • Hiroki Asakawa

    (Faculty of Science and Engineering, Chuo University)

  • Ka-Ho Lee

    (The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong)

  • Zhenyang Lin

    (The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong)

  • Makoto Yamashita

    (Faculty of Science and Engineering, Chuo University)

Abstract

Transition metal reagents and catalysts are generally effective to cleave all three bonds (one σ and two π) in a triple bond despite its high bonding energy. Recently, chemistry of single-bond cleavage by using main-group element compounds is rapidly being developed in the absence of transition metals. However, the cleavage of a triple bond using non-transition-metal compounds is less explored. Here we report that an unsymmetrical diborane(4) compound could react with carbon monoxide and tert-butyl isonitrile at room temperature. In the latter case, the carbon–nitrogen triple bond was completely cleaved in the absence of transition metal as confirmed by X-ray crystallographic analysis, 13C NMR spectroscopy with 13C labelling and DFT calculations. The DFT calculations also revealed the detailed reaction mechanism and indicated that the key for the carbon–nitrogen triple-bond cleavage could be attributed to the presence of nucleophilic nitrogen atom in one of the intermediates.

Suggested Citation

  • Hiroki Asakawa & Ka-Ho Lee & Zhenyang Lin & Makoto Yamashita, 2014. "Facile scission of isonitrile carbon–nitrogen triple bond using a diborane(4) reagent," Nature Communications, Nature, vol. 5(1), pages 1-9, September.
    • Handle: RePEc:nat:natcom:v:5:y:2014:i:1:d:10.1038_ncomms5245
    DOI: 10.1038/ncomms5245
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