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Post-assembly reactivity of N-aryl iminoboronates: Reversible radical coupling and unusual B-N dynamic covalent chemistry

DOI: 10.1002/chem.201802790 DOI Help

Authors: Evan Keyzer (University of Cambridge) , Alexandru Sava (University of Cambridge) , Tanya Ronson (University of Cambridge) , Jonathan Nitschke (University of Cambridge) , Anna Mcconnell (University of Kiel)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Chemistry - A European Journal

State: Published (Approved)
Published: July 2018
Diamond Proposal Number(s): 8464

Open Access Open Access

Abstract: 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+.

Journal Keywords: dynamic covalent chemistry; iminoboronate; radical coupling; post-assembly; supramolecular

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 05/07/2018 16:04


Discipline Tags:

Chemistry Chemical Engineering Engineering & Technology

Technical Tags:

Diffraction Single Crystal X-ray Diffraction (SXRD)