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Ambiphilic boron in 1,4,2,5-diazadiborinine

Author

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  • Baolin Wang

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

  • Yongxin Li

    (NTU-SPMS-CBC Crystallography Facility, Nanyang Technological University)

  • Rakesh Ganguly

    (NTU-SPMS-CBC Crystallography Facility, Nanyang Technological University)

  • Hajime Hirao

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

  • Rei Kinjo

    (School of Physical and Mathematical Sciences, Nanyang Technological University)

Abstract

Boranes have long been known as the archetypal Lewis acids owing to an empty p-orbital on the boron centre. Meanwhile, Lewis basic tricoordinate boranes have been developed in recent years. Here we report the synthesis of an annulated 1,4,2,5-diazadiborinine derivative featuring boron atoms that exhibit both Lewis acidic and basic properties. Experimental and computational studies confirmed that two boron atoms in this molecule are spectroscopically equivalent. Nevertheless, this molecule cleaves C–O, B–H, Si–H and P–H bonds heterolytically, and readily undergoes [4+2] cycloaddition reaction with non-activated unsaturated bonds such as C=O, C=C, C≡C and C≡N bonds. The result, thus, indicates that the indistinguishable boron atoms in 1,4,2,5-diazadiborinine act as both nucleophilic and electrophilic centres, demonstrating ambiphilic nature.

Suggested Citation

  • Baolin Wang & Yongxin Li & Rakesh Ganguly & Hajime Hirao & Rei Kinjo, 2016. "Ambiphilic boron in 1,4,2,5-diazadiborinine," Nature Communications, Nature, vol. 7(1), pages 1-10, September.
  • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms11871
    DOI: 10.1038/ncomms11871
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