The Dynamic Covalent Chemistry of Amidoboronates: Tuning the rac5/rac6 Ratio via the B-N and B-O Dynamic Covalent Bonds

27 January 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Amidoboronates were prepared as a mixture of up to three isomers (rac5, meso5 and rac6) from the reductive coupling of N-aryl iminoboronates with either cobaltocene or decamethylcobaltocene in acetonitrile. The interconversion of rac5 and rac6 isomers via rearrangement of their dynamic covalent B N bonds was investigated in solution by redissolving isolated crystals. The aniline para substituent and catechol within the amidoboronates tuned the distribution between the rac5 and rac6 isomers; the rac6 isomer predominated for amidoboronates based on pyrocatechol with electron-withdrawing substituents and no interconversion was observed for the rac5 isomers of amidoboronates based on tetrachlorocatechol. Furthermore, the rac5/rac6 distribution was altered by catechol exchange of pyrocatechol for tetrachlorocatechol exploiting the dynamic covalent B O bonds.


radical coupling
dynamic covalent chemistry
supramolecular chemistry

Supplementary materials

Supporting Information
Synthesis and characterisation details


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