Single-Nitrogen Atom Incorporation into B=B Bond via the N=N Bond Splitting of Diazo Compound and Diazirine |
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Authors: | Dr Lizhao Zhu Prof Dr Rei Kinjo |
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Institution: | School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Nanyang Link 21, Singapore, 637371 Singapore |
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Abstract: | Triboraazabutenyne 3 is synthesized by the reaction of diboraazabutenyne 1 with aryl boron dibromide followed by the reduction. The ligand exchange to replace phosphine on the terminal sp2 B atom with carbene furnishes 4 . 11B NMR, solid-state structures, and computational studies disclose that 3 and 4 feature the extremely polarized B=B bond. 4 readily splits the N=N bond of both diazo compound and diazirine under ambient conditions, whereby one nitrogen atom is incorporated into the B=B moiety leading to a neutral diboraazaallene 6 . The mechanism of the reaction between 4 and diazo compound is extensively investigated by density functional theory (DFT) calculations, as well as the isolation of an intermediate. |
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Keywords: | B−B Unsaturated Bond Bond Activation Diazirine Diazo Compound Single-N Atom Incorporation |
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