Sunlight decatungstate photoinduced trifluoromethylations of (hetero)aromatics and electron-poor olefins

Corsico, Sara; Fagnoni, Maurizio; Ravelli, Davide

doi:10.1039/c7pp00179g

Cited by 27 publications

(20 citation statements)

References 46 publications

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“…Based on the above results and previous literature, a plausible mechanistic interpretation is depicted in Scheme 3[22,[24][25][26][27][28][29][30][31]. Initially, CF 3 SO 2…”

supporting

confidence: 63%

“…When a radical inhibitor, including TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) and BHT (butylated hydroxytoluene), was added, the reaction was dramatically suppressed, implying that a radical reaction pathway might be involved in the catalytic cycle. Based on the above results and previous literature, a plausible mechanistic interpretation is depicted in Scheme 3 [22,[24][25][26][27][28][29][30][31]. Initially, CF3SO2 -reacts with t BuOOH to form •CF3 (A).…”

Section: Resultsmentioning

confidence: 59%

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Cu(II)-Catalyzed Oxidative Trifluoromethylation of Indoles with KF as the Base

Shi

2019

Catalysts

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This paper offers an efficient copper-catalyzed oxidative trifluoromethylation of indoles with low-cost CF3SO2Na via C–H activation. Notably, the use of a base is crucial for the trifluoromethylation of indoles. This reaction proceeds efficiently in good to excellent yields and is tolerance of a broad range of functional groups. Furthermore, melatonin, a medicine for sleep disorders, is converted to its 2-CF3 analogue in 68% yield. Studies of possible reaction pathways suggest that this reaction proceeds through a radical process.

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“…Based on the above results and previous literature, a plausible mechanistic interpretation is depicted in Scheme 3[22,[24][25][26][27][28][29][30][31]. Initially, CF 3 SO 2…”

supporting

confidence: 63%

Section: Resultsmentioning

confidence: 59%

Cu(II)-Catalyzed Oxidative Trifluoromethylation of Indoles with KF as the Base

Shi

2019

Catalysts

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“…Córsico and Ravelli [7a] have informed the trifluoromethylation of alkoxy‐substituted (hetero)arenes employing tetrabutylammonium decatungstate (TBADT) as photocatalyst, the Langlois reagent (NaSO 2 CF 3 ) as source of CF 3 radicals in the presence of K 2 S 2 O 8 as oxidant, in MeCN : water mixture, irradiating with a solar lamp (Scheme 1).…”

Section: Discussionmentioning

confidence: 99%

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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“…Figure 4b elow summarizes previously reviewed and informed visible-light-photocatalyzed approaches for trifluoromethylation reactions of (hetero)aromaticc ompounds.T he known and reviewed strategies involveo rganometallic photocatalysts( Figure 4A)w hich employ triflic chloride, [22,23] To gni reagent, [31,32] CF 3 I, [29, 30c] and Langlois reagent. [36,37] Figure 4B,s how all the reportedn onmetal organo-photocatalysts that make use of the Langlois reagent, [34, 35 ,38-40] triflic chloride, [32,41] To gni reagent, [32,42] and CF 3 I [33] as sourcesofC F 3 radicals.…”

Section: (Hetero)aromatic Substratesmentioning

confidence: 99%

New Visible‐Light‐Triggered Photocatalytic Trifluoromethylation Reactions of Carbon–Carbon Multiple Bonds and (Hetero)Aromatic Compounds

Barata‐Vallejo

Postigo

2020

Chemistry A European J

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Visible‐light‐photocatalyzed methods employed in synthetic transformations present attractive properties such as environmentally friendly, safety, availability and excellent functional group tolerance. In this regard, research on the visible‐light photocatalytic incorporation of the trifluoromethyl CF3 moiety into organic substrates, in particular, has contributed to a clear evolution of the field of photocatalysis. Although this particular area is constantly evolving and has been reviewed, the last five years have experienced an outburst of seminal and significant photocatalytic trifluoromethylation examples that are leading the way and opening new synthetic avenues. Recent review articles on Ru‐ and Ir‐based photocatalytic trifluoromethylation reactions have borne witness of this evolution. Although this account will show the new Ru‐ and Ir‐based photocatalytic trifluoromethylations, Sections 2 and 3 will also illustrate other photocatalytic systems, such as organic dyes, organic semiconductors and newly‐developed all‐organic photocatalysts. All the known and reviewed strategies for photocatalytic trifluoromethylation reactions of olefins and (hetero)aromatic compounds will not be discussed but will be summarized in two figures (Figures 4 and 5), and new examples (2015–present) will be presented and discussed.

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Sunlight decatungstate photoinduced trifluoromethylations of (hetero)aromatics and electron-poor olefins

Cited by 27 publications

References 46 publications

Cu(II)-Catalyzed Oxidative Trifluoromethylation of Indoles with KF as the Base

Cu(II)-Catalyzed Oxidative Trifluoromethylation of Indoles with KF as the Base

Catalytic Fluoroalkylation Reactions of Alkoxy‐substituted (Hetero)Arenes

New Visible‐Light‐Triggered Photocatalytic Trifluoromethylation Reactions of Carbon–Carbon Multiple Bonds and (Hetero)Aromatic Compounds

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