gem‐Difluorocyclopropanes (F2CPs) have aroused considerable attention not only from the structural perspective but also due to their ability to participate in various valuable transformations. This Review summarizes advances in catalytic ring‐opening reactions of gem‐F2CPs, especially emphasizing the reactivities and applications of those non‐activated ones under transition‐metal catalysis. Their achievements, synthetic applications and limitations are discussed with the aim to stimulate enthusiasm for further development.

Catalytic Diversification of gem‐Difluorocyclopropanes: Recent Advances and Challenges

Direct Hydrodefluorination of CF3-Alkenes via a Mild SN2' Process Using Rongalite as a Masked Proton Reagent.

Organic fluorine compounds are ubiquitous and pivotally important organic molecules, yet their activation and transformation have long been a formidable challenge due to the high energy and low reactivity of C—F bonds. Organic electrosynthesis, an environmentally benign synthetic method in organic chemistry, enables a myriad of chemical transformations without the need for external redox reagents. In recent years, organic electrochemistry has emerged as a powerful tool for achieving the activation and transformation of C—F bonds in fluorine‐containing compounds. This review aims to succinctly recapitulate the latest advancements in the electrochemical defluorinative transformations of C—F bonds and to delve into the reaction design, mechanistic insights, and developmental prospects of these methods.
In 1959, Lund was the first to pioneer the electroreduction of CF3 to CH3 group. Electrochemistry has lately provided new opportunities for efficient conversion of organic fluorides. In 2020, Zhou and coworkers discovered the electrochemical defluorinative carboxylation of α‐CF3 alkenes. Lambert and colleagues reported electrophotocatalytic defluorinative amination of aryl fluorides. Electrochemical hydrodefluorination of trifluoromethylketones was developed by Lennox and coworkers in 2021. In the same year, Wang and Guo disclosed electrochemical radical defluorinative alkylation of α‐CF3 alkenes with Katritzky salts as the alkyl radical precursors. Subsequently, Wu and Liao described a transition‐metal‐free, site‐selective C—F arylation of polyfluoroarenes with (het)arenes using paired electrophotocatalysis. In 2023, numerous efforts were made to achieve electrochemical C—F bond activation. Xia and Guo developed an organoboron‐controlled method for the chemoselective electrochemical sequential (deutero)hydrodefluorination of trifluoroacetamides.


Recent Advances in the Electrochemical Defluorinative Transformations of C—F Bonds

A metal free, visible-light driven α-C(sp 3 )−H gem-difluoroallylation of glycine derivatives with CF 3 -alkenes and 1,3-enynes is presented under redox-neutral conditions with good yields and excellent functional group compatibility. 

Metal-free, visible-light driven α-C(sp3)–H gem-difluoroallylation of glycine derivatives with trifluoromethyl alkenes and 1,3-enynes

Fluorine and fluoroalkyl groups wildly exist in organic molecules that are useful in numerous fields such as biological chemistry, medicinal science, agrochemistry, materials science and synthetic chemistry. The efficient modification...

Recent advances in N-heterocyclic carbene (NHC) catalyzed fluorination and fluoroalkylation

HP(O)Ph2/H2O-Promoted Hydrodefluorination of Trifluoromethyl Alkenes

The latest achievements in transition-metal-catalyzed enantioselective defluorinative coupling reactions have been comprehensively summarized on the basis of the classification of transition-metal catalysts.

Transition-metal-catalyzed asymmetric defluorinative reactions

Four-Component Defluorinative Reaction of Allylic Fluorides, Amidines, and Cs2CO3 under Transition-Metal-Free Conditions

DMSO-Promoted Difluoroalkylation of Organophosphonium Salts with Difluoroenol Silyl Ethers.

A H2O-promoted and (NH4)2CO3-enabled deiodoamination and defluoroiminizative reaction of fluoroalkyl alkenes has been developed under transition-metal-free conditions. Structurally important fluoroalkylated 1,5-diazapentadienes were obtained in excellent Z-selectivity with good functional group...

Water-Promoted Defluorinative Synthesis of Fluoroalkylated 1,5-Diazapentadienes by Using (NH4)2CO3 as NH2 and NH Sources

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