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

Hiroki Asakawa, Ka-Ho Lee, Zhenyang Lin () and Makoto Yamashita ()
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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

Nature Communications, 2014, vol. 5, issue 1, 1-9

Abstract: 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.

Date: 2014
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DOI: 10.1038/ncomms5245

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