Abstract
Among the realm of visible light photocatalytic transformations, late-stage difluoromethylation reactions (introduction of difluoromethyl groups in the last stages of synthetic protocols) have played relevant roles as the CF2X group substitutions exert positive impacts on the physical properties of organic compounds including solubility, metabolic stability, and lipophilicity, which are tenets of considerable importance in pharmaceutical, agrochemical, and materials science. Visible-light-photocatalyzed difluoromethylation reactions are shown to be accomplished on (hetero)aromatic and carbon–carbon unsaturated aliphatic substrates under mild and environmentally benign conditions.
Highlights
The relevance of organofluorine compounds spans areas of considerable importance such as pharmaceutical, agrochemical, and materials science, as the introduction of fluoro-substituents into these types of molecules has a striking positive impact on their physical properties including metabolic stability, solubility, and lipophilicity
The phosphonodifluoromethylation of alkenesMultiple has been documented to proceed through diverse methods such as nucleophilic addition [47,48,49,50,51,52,53,54], transition metal catalysis [55,56,57,58], photoredox catalysis
A practical method for the synthesis of difluoromethylated through visible-light induced radical difluoromethylation of β,γ-unsaturated oximes hasisoxazolines been published by Zhu et al [81]
Summary
The relevance of organofluorine compounds spans areas of considerable importance such as pharmaceutical, agrochemical, and materials science, as the introduction of fluoro-substituents into these types of molecules has a striking positive impact on their physical properties including metabolic stability, solubility, and lipophilicity. The difluoromethyl group has garnered particular attention in medicinal chemistry due to the fact that the CF2 H moiety is isosteric and isopolar to the –OH and –SH groups, acting as a lipophilic hydrogen bond donor. This simultaneously harnesses the electronegativity of the fluorine atoms to emulate the oxygen (or sulfur) lone electron pairs, while rendering the methane proton acidic and a competent hydrogen bond donor [1].
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