B-B Cleavage and Ring-Expansion of a 1,4,2,3-Diazadiborinine with N-Heterocyclic Carbenes.

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ID: 56905
2019
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Abstract
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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Authors Thiess, Torsten;Mellerup, Soren K;Braunschweig, Holger;
Journal Chemistry (Weinheim an der Bergstrasse, Germany)
Year 2019
DOI
10.1002/chem.201903259
URL
Keywords
b,n-heterocycles b−b bond activation nhcs diazadiborinines ring-expansion reactions

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