Post-Assembly Reactivity of N-Aryl Iminoboronates: Reversible Radical Coupling and Unusual B-N Dynamic Covalent Chemistry.
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Keyzer, E., Sava, A., Ronson, T., Nitschke, J., & McConnell, A. J. (2018). Post-Assembly Reactivity of N-Aryl Iminoboronates: Reversible Radical Coupling and Unusual B-N Dynamic Covalent Chemistry.. Chemistry, 24 (46), 12000-12005. https://doi.org/10.1002/chem.201802790
Post-assembly reaction of a dynamic covalent iminoboronate system following addition of Cp2 Co resulted in the formation of a series of new reductively coupled dianionic dimers via C-C bond formation. The dimers formed as a mixture of BN-containing isomeric products: diastereomers rac5 and meso5, with coupled five-membered rings, and enantiomeric rac6, with a fused six-membered ring bicyclic system from C-C bond formation and rearrangement of the B-N bonds. Each isomer was identified using 1 H NMR spectroscopy in combination with single crystal X-ray structure determination. Interestingly, interconversion between the coupled five-membered rings (rac5 ) and fused bicyclic systems (rac6 ) was found to occur through an unprecedented breaking and reforming of the B-N covalent bond. Further, the coupled products could be converted quantitatively back to their iminoboronate precursors with addition of the electron abstractor Ph3 C+ .
European Research Council (695009) EPSRC (EP/M01083X/1)
Engineering and Physical Sciences Research Council (EP/M01083X/1)
European Research Council (695009)
External DOI: https://doi.org/10.1002/chem.201802790
This record's URL: https://www.repository.cam.ac.uk/handle/1810/284531
Attribution 4.0 International
Licence URL: https://creativecommons.org/licenses/by/4.0/