Stereodefined Synthesis of 3-Difluoromethyl-Benzoxaboroles: Novel Antimicrobials with Unlocked H-Bonding
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 -CHF<sub>2</sub> preserves stability while promoting bioactivity, owing to the lipophilic H-bond donor properties of the latter.
Authors
- Valerio Fasano (ORCID: https://orcid.org/0000-0003-1819-4483)
- Andrea Citarella (ORCID: https://orcid.org/0000-0001-5881-7142)
- Daniele Passarella (ORCID: https://orcid.org/0000-0001-6180-9581)
- Valerio Baldelli (ORCID: https://orcid.org/0000-0001-6698-7061)
- Paolo Ronchi
- Alessandro Dimasi (ORCID: https://orcid.org/0009-0008-0211-9327)
- Giovanni Macetti (ORCID: https://orcid.org/0000-0001-9935-7955)
- Valentina Mileo
- Francesco Castagnini (ORCID: https://orcid.org/0000-0002-3567-9194)
- Elio Rossi (ORCID: https://orcid.org/0000-0002-2042-608X)
- Arianna Montoli (ORCID: https://orcid.org/0009-0008-1317-2158)
- Claudio Lutti
- Paolo Landini
Institutions
- University of Parma (IT)
- University of Milan (IT)
- Chiesi Foundation (IT)
- Chiesi (France) (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-01-22
- DOI
- https://doi.org/10.1021/acs.orglett.5c04602
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Chiesi Farmaceutici
- Università degli Studi di Milano
- Papua New Guinea University of Technology