Recent advance in the C–F bond functionalization of trifluoromethyl-containing compounds

Yan, Guobing; Qiu, Kaiying; Guo, Ming

doi:10.1039/d1qo00037c

Cited by 136 publications

(61 citation statements)

References 145 publications

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“…Consequently, most examples of CF 3 group activation involve a CF 3 group connected to an sp 2 carbon atom, typically an electron-deficient aromatic ring or a carbonyl group (Scheme 7a). 69…”

Section: Preparation Of Fluoro-grignard Reagentsmentioning

confidence: 99%

Grignard reagent formation via C–F bond activation: a centenary perspective

Pietrasiak

Lee

2022

Chem. Commun.

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Section: Preparation Of Fluoro-grignard Reagentsmentioning

confidence: 99%

Grignard reagent formation via C–F bond activation: a centenary perspective

Pietrasiak

Lee

2022

Chem. Commun.

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“…The use of electrochemistry because of its essential attributes was widely used in electro‐organic synthesis for procuring important motifs. Eventually, the electrochemical synthesis has paved the way for the synthesis of nitrile [84–87] . The simple and mild reaction conditions, more accessible methods of handling, high atom efficiency with the more energy‐saving options electrochemical synthesis is progressing in recent years.…”

Section: Introductionmentioning

confidence: 99%

“…Eventually, the electrochemical synthesis has paved the way for the synthesis of nitrile. [84][85][86][87] The simple and mild reaction conditions, more accessible methods of handling, high atom efficiency with the more energy-saving options electrochemical synthesis is progressing in recent years.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Electrochemical Synthesis of Nitriles: A Sustainable Approach

et al. 2022

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Nitriles unveil widespread applications in pharmaceuticals, agrochemicals, textiles, rubber, polymers, and constitute a significant intermediate in several organic transformations, necessitating the design of simple and environmentally benign pathways for their synthesis. Over the recent years, electro‐organic reactions have found widespread attention in developing effective and selective organic synthesis. They possess several advantages: high atom economy, selectivity, minimal waste production, and shorter routes to multistep traditional organic reactions. The development of novel strategies for greener and sustainable electro‐organic synthesis of nitriles is therefore commendable. This review focuses on analyzing various methods and strategies used in the electrochemical synthesis of nitriles using phase transfer catalyst, N‐oxoammonium salts mediated electrocatalysis, iodine‐mediated electrocatalysis, and anodic oxidations of aldoximes. In addition, the recent trends including the synthesis of nitriles via C−H cyanation, domino oxidation, bio electrocatalysis, and metal‐ligand cooperative synthesis have been discussed.

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“…Therefore, we feel justified in again reviewing the topic with the same focus that characterized our earlier review. Although there have been several reviews on C-F bond cleavage recently, each review has its specific focus, such as C-F bond activation by phosphorus compounds [25], or by metalloenzymes [26], C-F functionalization of trifluoromethyl groups [27,28], catalytic enantioselective functionalization of allylic C-F bond [29], transition metal-catalyzed C(sp 2 )-F cleavage [30], and deconstructive modes of halodifluoromethyl reagents [31]. This review focuses on the C-F bond cleavage enabled by visible light photoredox catalysis since 2018, classified by the types of fluorosubstrates [32,33].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis

Zhou

2021

Molecules

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The creation of new bonds via C-F bond cleavage of readily available per- or oligofluorinated compounds has received growing interest. Using such a strategy, a myriad of valuable partially fluorinated products can be prepared, which otherwise are difficult to make by the conventional C-F bond formation methods. Visible light photoredox catalysis has been proven as an important and powerful tool for defluorinative reactions due to its mild, easy to handle, and environmentally benign characteristics. Compared to the classical C-F activation that proceeds via two-electron processes, radicals are the key intermediates using visible light photoredox catalysis, providing new modes for the cleavage of C-F bonds. In this review, a summary of the visible light-promoted C-F bond cleavage since 2018 was presented. The contents were classified by the fluorosubstrates, including polyfluorinated arenes, gem-difluoroalkenes, trifluoromethyl arenes, and trifluoromethyl alkenes. An emphasis is placed on the discussion of the mechanisms and limitations of these reactions. Finally, my personal perspective on the future development of this rapidly emerging field was provided.

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Recent advance in the C–F bond functionalization of trifluoromethyl-containing compounds

Abstract: The C-F bond is the strongest single bond in organic compounds. It is the most challenging task to study the activation of C-F bond in organic synthesis. Trifluoromethyl-containing compounds, which...

Cited by 136 publications

References 145 publications

Grignard reagent formation via C–F bond activation: a centenary perspective

Grignard reagent formation via C–F bond activation: a centenary perspective

Recent Advances in Electrochemical Synthesis of Nitriles: A Sustainable Approach

Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis

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