Journal
CHEMICAL SCIENCE
Volume 11, Issue 27, Pages 7053-7059Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc02162h
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Funding
- Natural Science Foundation of China [21971144, 21702228, 21673301]
- Natural Science Foundation of Shandong Province [ZR2019ZD46, ZR2017MB021]
- Key R&D Program of Shandong Province [2019GGX102032]
- Guangdong Natural Science Funds for Distinguished Young Scholars [2015A030306027]
- Qilu Youth Scholar Funding of Shandong University [11190088963021]
- Multidisciplinary Research and Innovation Team of Young Scholars of Shandong University [2020QNQT007]
- Fundamental Research Funds for the Central Universities
- SUSTech
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The mono-base-stabilized 1,2-diboranylidenehydrazine derivatives featuring a 1,3-dipolar BNN skeleton are obtained by dehydrobromination of [ArB(Br)NH](2)(Ar = 2,6-diphenylphenyl (Dpp), Ar = 2,6-bis(2,4,6-trimethylphenyl)phenyl (Dmp) or Ar = 2,4,6-tri-tert-butylphenyl (Mes*)) with N-heterocyclic carbenes (NHCs). Depending on the Ar substituents, such species can be isolated as a crystalline solid (Ar = Mes*) or generated as reactive intermediates undergoing spontaneous intramolecular aminoboration of the proximal arene ringsvia[3 + 2] cycloaddition (Ar = Dpp or Dmp). The latter reactions showcase the 1,3-dipolar reactivity toward unactivated arenes at ambient temperature. In addition, double cycloaddition of the isolable BNN species with two CO(2)molecules affords a bicyclic species consisting of two fused five-membered BN2CO rings. The electronic structures of these BNN species and the mechanisms of these cascade reactions are interrogated through density functional theory (DFT) calculations.
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