Direct C-H Electrophilic Borylation with (C6F5)2B-NTf2 to Generate B-N Dibenzo[a,h]pyrenes

20 February 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The borylation of aryl substituted pyridines is an effective way of preparing B-N doped conjugated organic frameworks. Trihaloborane Lewis acids are often employed for this protocol, and may require further functionalization to replace the remaining halides on boron. We report a new, fully characterized, electrophilic borylating agent, (C6F5)2B(2-NTf2), that smoothly incorporates a -B(C6F5)2 unit into the model substrate 2-phenylpyridine. To demonstrate its utility in preparing more complex B-N doped structures, we use it to prepare seven examples of the 6a,13a-diaza-7,14-dibora-dibenzo[a,h]pyrene framework, with substituents of varying donor properties. The structural, redox and photophysical properties of this new family of B-N doped polycyclic hydrocarbon compounds were probed experimentally and computationally.


fluoroaryl boranes
boron-nitrogen doped polycyclic aromatic materials
organoboron compounds


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