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, (13)C NMR spectroscopy with (13)C 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.
journal_name
Nat Communjournal_title
Nature communicationsauthors
Asakawa H,Lee KH,Lin Z,Yamashita Mdoi
10.1038/ncomms5245subject
Has Abstractpub_date
2014-06-26 00:00:00pages
4245issn
2041-1723pii
ncomms5245journal_volume
5pub_type
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