NDLI: Post‐Assembly Reactivity of N ‐Aryl Iminoboronates: Reversible Radical Coupling and Unusual B−N Dynamic Covalent Chemistry

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Post‐Assembly Reactivity of N ‐Aryl Iminoboronates: Reversible Radical Coupling and Unusual B−N Dynamic Covalent Chemistry

Content Provider	Scilit
Author	Keyzer, Evan N. Sava, Alexandru Ronson, Tanya K. Nitschke, Jonathan R. McConnell, Anna J.
Copyright Year	2018
Description	Journal: Chemistry – A European Journal Post‐assembly reaction of a dynamic covalent iminoboronate system following addition of Cp2Co resulted in the formation of a series of new reductively coupled dianionic dimers via C‐C bond formation. The boronate 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 1H 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 Ph3C+.
Related Links	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6175077/pdf
Ending Page	12005
Page Count	6
Starting Page	12000
e-ISSN	15213765
DOI	10.1002/chem.201802790
Journal	Chemistry – A European Journal
Issue Number	46
Volume Number	24
Language	English
Publisher	Wiley-Blackwell
Publisher Date	2018-06-25
Access Restriction	Open
Subject Keyword	Journal: Chemistry – A European Journal Organic Chemistry Dynamic Covalent Chemistry
Content Type	Text
Resource Type	Article

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