Work

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

Year: 2025

Type: article

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.

Source: Chemical Communications

DOI: 10.1039/d5cc05350a

Authors: Pankaj Kumar, Leah Mistry, Josephine M. Stewart, Graham Pattison

Institutions: University of Lincoln, University of St Andrews

Language: English

Topic: Organoboron and organosilicon chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Funder: Engineering and Physical Sciences Research Council

Award: Synthesis of enolates by nucleophilic substitution