Photoredox Catalytic Trifluoromethylation and Perfluoroalkylation of Arenes Using Trifluoroacetic and Related Carboxylic Acids

Yin, Duanzhi; Su, De-Bao; Jin, Jian

doi:10.1016/j.xcrp.2020.100141

Cited by 49 publications

(34 citation statements)

References 85 publications

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“…Jin, Yin and colleagues [13] used a diarylsulfoxide activator to produce CF 3 radicals from trifluoroacetic acid TFA through photocatalysis. This source of CF 3 radicals (i. e.: TFA) is rarely used on account of the high oxidation potential of TFA (>2.5 V vs SCE) to produce the trifluoroacetate radicals.…”

Section: Discussionmentioning

confidence: 99%

“…The activator used by the authors [13] was bis(4‐chlorophenyl)sulfoxide, which upon oxidative ET from excited Ru(bpy) 3 Cl 2 afforded intermediate I (Scheme 5). Intermediate I underwent electron reduction to afford CF 3 radicals, SO 2 and diarylsulfide.…”

Section: Discussionmentioning

confidence: 99%

“…On the other hand, photocatalytic methods, [7,8,13] employed for fluoroalkylation of alkoxy‐substituted (hetero)arenes, although more environmentally benign, also vary significantly in terms of reactions conditions. Photocatalytic methods requiring an oxidant [7] are sensitive to the presence of oxidizable groups pre‐assembled on the molecule.…”

Section: Summarizing Tablementioning

confidence: 99%

“…Photocatalytic methods requiring an oxidant [7] are sensitive to the presence of oxidizable groups pre‐assembled on the molecule. Photocatalytic methods relying on commercially available inexpensive fluoroalkylating reagents, such as trifluoracetic acid [13] are promising, and less expensive than other methods needing the Langlois reagent [7] or perfluoroalkyl iodides [8] . A compromise should be made between product yields and environmental demand of the protocols to be employed.…”

Section: Summarizing Tablementioning

confidence: 99%

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Catalytic Fluoroalkylation Reactions of Alkoxy‐substituted (Hetero)Arenes

et al. 2021

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Electron‐rich alkoxy‐substituted (hetero)arenes and electrophilic fluoroalkyl moieties represent advantageous partners for substitution reactions due to their electronic match. Fluoroalkylation strategies of alkoxy‐substituted (hetero)arenes are herein presented which depict photocatalytic and thermal methods. Photocatalytic methods rely on the use of diverse photocatalysts such as Ru(bpy)3Cl2, tetrabutylammonium decatungstate TBADT, N‐doped carbon nanodots NCNDs, and vitamin derivatives which can partner with the Langlois reagent NaSO2CF3, CF3CO2H, and perfluoroalkyl iodides RF‐I as fluoroalkylating reagents. Also, electrocatalytic methods that make use of the cathodic reduction of CF3SO2Cl to generate CF3 radicals can achieve trifluoromethylation reactions of alkoxy‐substituted (hetero)arenes. On the other hand, thermal methodologies comprising Pd(OAc)2 catalysis and using CF3Br as trifluoromethylating source have been implemented.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Summarizing Tablementioning

confidence: 99%

Section: Summarizing Tablementioning

confidence: 99%

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Catalytic Fluoroalkylation Reactions of Alkoxy‐substituted (Hetero)Arenes

et al. 2021

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“…fache freie Carbonsäuren wie Trifluoressigsäure in Gegenwart von Sulfoxiden unter photokatalytischen Bedingungen -auch sie liefern das gewünschte • CF 3 -Radikal (Abbildung 3i). 20)…”

Section: Auf Einen Blickunclassified

Strategien bei radikalischen Trifluormethylierungen

Didier¹,

Reiners²

2021

Nachr Chem

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Direct CH Difluoroalkylation and Perfluoroalkylation of Heteroarenes

Fruit¹

2022

Handbook of CH-Functionalization

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This article summarizes the main recent achievements reported in transition metal‐catalyzed and metal‐free CH difluoromethylation and perfluoroalkylation using various fluoroalkyl‐coupling partners over the past decade, for constructing high‐valuable fluoro‐containing heteroarenes. This resume is mainly categorized based on different catalytic systems for each fluoroalkylation reaction. Difluoroalkylation that involves a metal‐catalyzed or a visible‐light‐induced reaction will be addressed first. Following this, the direct perfluoroalkylation of CH bonds under various reaction conditions will be covered. The overall aim is to paint a picture of the state of the art in difluoro‐ and perfluoroalkylation chemistry for medicinal chemists and point out how the recent innovative strategies have been able to positively affect the synthesis of new bioactive compounds.

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Photoredox Catalytic Trifluoromethylation and Perfluoroalkylation of Arenes Using Trifluoroacetic and Related Carboxylic Acids

Cited by 49 publications

References 85 publications

Catalytic Fluoroalkylation Reactions of Alkoxy‐substituted (Hetero)Arenes

Catalytic Fluoroalkylation Reactions of Alkoxy‐substituted (Hetero)Arenes

Strategien bei radikalischen Trifluormethylierungen

Direct CH Difluoroalkylation and Perfluoroalkylation of Heteroarenes

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