# Stereodefined Synthesis of 3‑Difluoromethyl-Benzoxaboroles: Novel Antimicrobials with Unlocked H‑Bonding

## TL;DR

Researchers created a new type of benzoxaborole compound with a difluoromethyl group that is stable and has potential antimicrobial properties.

## Contribution

The novel synthesis of stereodefined 3-difluoromethyl-benzoxaboroles with enhanced stability and bioactivity is introduced.

## Key findings

- Replacing the hydroxy group with a difluoromethyl group stabilizes the benzoxaborole structure.
- The new compound exhibits lipophilic H-bond donor properties that may enhance bioactivity.

## Abstract

Benzoxaboroles, prominent
scaffolds in medicinal chemistry, are
typically modified on the benzene ring. In contrast, functionalization
of the oxaborol ring is less common and often challenging. Indeed,
3-hydroxy-benzoxaboroles are virtually impossible to isolate due to
their tautomeric equilibrium with the carbonyl form. In this work,
we introduce a novel class of stereodefined 3-difluoromethyl-benzoxaboroles.
The replacement of the hydroxy group with −CHF2 preserves
stability while promoting bioactivity, owing to the lipophilic H-bond
donor properties of the latter.