Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 59, Pages 13572-13578Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903259
Keywords
B; N-heterocycles; B-B bond activation; diazadiborinines; NHCs; ring-expansion reactions
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Funding
- Julius-Maximilians-Universitat Wurzburg
- Deutsche Forschungsgemeinschaft (DFG)
- Government of Canada
- Alexander von Humboldt Foundation
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A 1,4,2,3-diazadiborinine derivative was found to form Lewis adducts with strong two-electron donors such as N-heterocyclic and cyclic (alkyl)(amino)carbenes. Depending on the donor, some of these Lewis pairs are thermally unstable, converting to sole B,N-embedded products upon gentle heating. The products of these reactions, which have been fully characterized by NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction, were identified as B,N-heterocycles with fused 1,5,2,4-diazadiborepine and 1,4,2-diazaborinine rings. Computational modelling of the reaction mechanism provides insight into the formation of these unique structures, suggesting that a series of B-H, C-N, and B-B bond activation steps are responsible for these intercalation reactions between the 1,4,2,3-diazadiborinine and NHCs.
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