Synthesis of ketones and mono-fluoro ketones via boron enolates formed by substitution of esters with benzylboronic esters

Abstract

Benzylboronic esters can be deprotonated using LiTMP and engaged in useful C–C bond-forming processes. Here we report that they undergo acylation with esters. We also report a fluorinative coupling reaction performed through nucleophilic substitution of a lithiated benzylboronic ester with an ester, and trapping of the resultant boron enolate with the fluorinating agent NFSI.