Litcius/Paper detail

Difluoroalkylation/Lactonization of Alkenes with <scp>BrCF<sub>2</sub>CO<sub>2</sub>K</scp> via Photoredox Catalysis: Access to α,<scp>α‐Difluoro</scp>‐γ‐lactones<sup>†</sup>

Min Zhang, Qiang Li, Jin‐Hong Lin, Ji‐Chang Xiao

2023Chinese Journal of Chemistry13 citationsDOIOpen Access PDF

Abstract

Comprehensive Summary Due to its unique electronic properties, the difluoromethylene group (CF 2 ) has served as a valuable unity in the design of biologically active molecules. Since γ‐lactones display a broad range of biological properties, α,α‐difluoro‐γ‐lactones may exhibit unexpected biological activities, and thus their synthesis has received increasing attention. Traditional synthetic methods suffer from tedious multi‐ step processes, and very few effective methods have been reported recently. Herein, we describe the difunctionalization of alkenes with BrCF 2 CO 2 K under photoredox catalysis with the use of a boron‐Lewis acid for the access to α,α‐difluoro‐γ‐lactones. In this transformation, the alkene substrates and the used reagents, including BrCF 2 CO 2 K and the boron‐Lewis acid, PhB(OH) 2 or BF 3 ·THF, are cheap and widely available. High efficiency and atom economy may make this protocol attractive.

Topics & Concepts

ChemistryCatalysisLewis acids and basesAlkeneBoronReagentCombinatorial chemistryAtom economyMoleculeLactoneStereochemistryMedicinal chemistryOrganic chemistryFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsRadical Photochemical Reactions