Use of Nitrogen‐Doped Carbon Nanodots for the Photocatalytic Fluoroalkylation of Organic Compounds

Rosso, Cristian; Filippini, Giacomo; Prato, Maurizio

doi:10.1002/chem.201903433

Cited by 39 publications

(40 citation statements)

References 57 publications

(102 reference statements)

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“…A plausible mechanism that drives the catalytic reaction by the am-CN is proposed on the basis of previous findings and supported by NMR studies (see below). Figure 4D shows the catalytic cycle, where before photo-induced charge separation in the semiconductor, the binding of 2a occurs presumably via halogen bonding with the N atoms of the photocatalyst (45). This step is of high importance, as it markedly affects the rate of the injection of the photo-excited electron into the C 4 F 9 I reagent and, thus, also the formation of the •C 4 F 9 radical (Ia).…”

Section: Resultsmentioning

confidence: 99%

Light-driven, heterogeneous organocatalysts for C–C bond formation toward valuable perfluoroalkylated intermediates

et al. 2020

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The favorable exploitation of carbon nitride (CN) materials in photocatalysis for organic synthesis requires the appropriate fine-tuning of the CN structure. Here, we present a deep investigation of the structure/activity relationship of CN in the photocatalytic perfluoroalkylation of organic compounds. Four types of CN bearing subtle structural differences were studied via conventional characterization techniques and innovative nuclear magnetic resonance (NMR) experiments, correlating the different structures with the fundamental mechanistic nexus and especially highlighting the importance of the halogen bond strength between the reagent and the catalyst surface. The optimum catalyst exhibited an excellent performance, with a very wide reaction scope, and could prominently trigger the model reaction using natural sunlight. The work lays a platform for establishing a new approach in the development of heterogeneous photocatalysts for organic synthesis related to medical, agricultural, and material chemistry.

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Section: Resultsmentioning

confidence: 99%

Light-driven, heterogeneous organocatalysts for C–C bond formation toward valuable perfluoroalkylated intermediates

et al. 2020

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“…Rosso, Filippini and Prato [8a] have come up with a perfluoroalkylation reaction of methoxy‐substituted arenes in the presence of N‐doped carbon nanodots (CND) by microwave‐assisted hydrothermal synthesis from arginine (Arg) and ethylenediamine, according to Figure 2.…”

Section: Discussionmentioning

confidence: 99%

“…The authors [8a] studied the reaction mechanism. Exclusion of light inhibited the reaction completely.…”

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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“…Moreover, in the following studies, we demonstrated that even nitrogen-doped carbon-based nanomaterials can serve as photocatalysts for the iodoperfluoroalkylation of organic compounds. [55][56][57] The mentioned purple light strategy was employed for the construction of a key intermediate in the synthesis of the breast cancer drug, namely Fulvestrant, in gram-scale (Method b, Figure 7).…”

Section: Iodoperfluoroalkylation Of Olefinsmentioning

confidence: 99%

Use of Perylene Diimides in Synthetic Photochemistry

2021

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Dedicated to Professor Franco Cozzi on the occasion of his 70th birthday. Perylene diimides (PDIs) are valuable organic chromophores that stand out for their outstanding optical and redox properties. Owing to these features, PDIs have emerged as prominent dyes capable of acting as photocatalysts for numerous relevant organic transformations. This Minireview highlights the recent advances in the application of PDIs in organic photocatalysis. The various mechanistic pathways of the photo-reduction reaction of aryl halides, recently proposed in independent studies, are discussed with an eye to unsolved challenges and forward-looking opportunities regarding the use of PDIs within this field.

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Use of Nitrogen‐Doped Carbon Nanodots for the Photocatalytic Fluoroalkylation of Organic Compounds

Cited by 39 publications

References 57 publications

Light-driven, heterogeneous organocatalysts for C–C bond formation toward valuable perfluoroalkylated intermediates

Light-driven, heterogeneous organocatalysts for C–C bond formation toward valuable perfluoroalkylated intermediates

Catalytic Fluoroalkylation Reactions of Alkoxy‐substituted (Hetero)Arenes

Use of Perylene Diimides in Synthetic Photochemistry

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