Nucleophilic substitution and acylation of benzylboronic esters yield ketones, indicating new C-C bond pathways.
Benzylboronic esters can be deprotonated using LiTMP and engaged in a range of useful C-C bond-forming processes. Here we report that they can undergo acylation with esters. We also report examples of fluorinative coupling reactions performed through nucleophilic substitution of a lithiated benzylboronic ester with an ester, and trapping of the resultant boron enolates with the electrophilic fluorinating agent NFSI.
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Kumar et al. (2025) studied this question.
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