Design and synthesis of Indol-PHOX: a new class of modular phosphine–oxazoline ligands for palladium-catalyzed enantioselective decarboxylative allylation
A novel class of chiral and modular P,N-ligands featuring an indolizine core (Indol-PHOX) has been developed, successfully enabling the highly efficient and enantioselective palladium-catalyzed decarboxylative allylation of various α-fluoro-β-ketoesters to access valuable α-allyl-α-fluoro ketones with yields up to 99% and 96% ee. This process exhibits a broad substrate scope, demonstrating good tolerance for both electron-withdrawing and electron-donating groups, as well as substitution patterns of the substrates. The reaction is scalable to the gram level, and subsequent post-functionalization reactions proceed successfully without erosion of enantiopurity.
Authors
- Tahar Ayad (ORCID: https://orcid.org/0000-0003-4210-5997)
- David Virieux (ORCID: https://orcid.org/0000-0002-6495-9478)
- Anzhela Karapetyan
- Phannarath Phansavath (ORCID: https://orcid.org/0000-0002-7854-170X)
- Virginie Ratovelomanana‐Vidal (ORCID: https://orcid.org/0000-0003-1167-1195)
- Laura Borrel
Institutions
- École Nationale Supérieure de Chimie de Montpellier (FR)
- Centre National de la Recherche Scientifique (FR)
- Chimie ParisTech - PSL (FR)
- Université de Montpellier (FR)
- Université Paris Sciences et Lettres (FR)
- Institut Charles Gerhardt Montpellier (FR)
Publication Details
- Journal
- RSC Advances
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ra04775g
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00