The direct introduction of diverse fluorinated motifs into feedstock molecules and advanced intermediates is widely studied in pharmaceutical research and drug development. Among the emerging motifs, the difluoromethyl CF2H is...

State of Knowledge in Photoredox-Catalysed Direct Difluoromethylation

A selection of perfluoroalkylation reactions of aliphatic substrates that display methodological and synthetic amplitude will be studied, giving examples of their applications and mechanistic details. An array of synthetic approaches for fluoroalkylation reactions are documented; in particular, radical protocols are prominent among perfluoroalkylation methods. To that effect, addition reactions of perfluoroalkyl radicals RF (RF=CnF2n+1, n > 1) to unsaturated organic substrates serve as one of the most direct and efficacious ways to access fluoroalkylated scaffolds. The syntheses of perfluoroalkyl-substituted vinyl, alkynyl, and allylic compounds; the syntheses of perfluoroalkyl-substituted hydro-, iodo-, and oxy-perfluoroalkylated alkanes and olefins; the syntheses of perfluoroalkyl-substituted carbonyl compounds; the syntheses of perfluoroalkyl-substituted enamides, amides, thioamides, and hydrazones; and multicomponent perfluoroalkylation reactions will be studied. While there are a number of accomplished reports on organofluorination, we aim to provide an overview of radical-involved perfluoroalkylation reactions of aliphatic substrates, covering examples from 2018 to early 2023, as summarized in Tables 1–4. 

Radical Perfluoroalkylation of Aliphatic Substrates

Perfluoroalkylated (hetero)arenes represent an extremely important family of molecules commonly utilized in many areas such as medicinal chemistry, agrochemistry and material sciences. Due to their unique properties, they have attracted significant interest from synthetic chemists and various methods have been developed for their synthesis. Among them, the direct perfluoroalkylation of C(sp 2 )-H bonds in (hetero)arenes is one of the most attractive and straightforward ones, provided that it proceeds with high levels of regioselectivity. In this review article, a comprehensive overview of advances in this field is presented, with a special focus on the reaction mechanisms involved in these transformations and their regioselectivity. All methods available have been classified according to the nature of the perfluoroalkyl chain introduced, trifluoromethylation reactions being overviewed in a separate section, and to the nature of the reagents/catalysts required.

/pdf/direct-perfluoroalkylation-of-c-h-bonds-in-hetero-arenes-1xv0abch.pdf

Direct Perfluoroalkylation of C-H Bonds in (Hetero)arenes.

Synthesis of Secondary Trifluoromethylated Alkyl Bromides Using 2-Bromo-3,3,3-trifluoropropene as a Radical Acceptor.

A straightforward access to trifluoromethylated natural products through late-stage functionalization.

Electrosynthesis can be considered a powerful and sustainable methodology for the synthesis of small organic molecules. Due to its intrinsic ability to generate highly reactive species under mild conditions by anodic oxidation or cathodic reduction, electrosynthesis is particularly interesting for otherwise challenging transformations. One such challenge is the installation of fluorinated alkyl groups, which has gained significant attention in medicinal chemistry and material science due to their unique physicochemical features. Unsurprisingly, several electrochemical fluoroalkylation methods have been established. In this review, we survey recent developments and established methods in the field of electrochemical mono-, di-, and trifluoromethylation, and perfluoroalkylation of small organic molecules.

Electrochemical Installation of CFH2-, CF2H-, CF3-, and Perfluoroalkyl Groups into Small Organic Molecules

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Electrochemical Installation of CFH2-, CF2H-, CF3-, and Perfluoroalkyl Groups into Small Organic Molecules