Carbon-to-nitrogen single-atom transmutation of azaarenes

Nature, Journal Year: 2023, Volume and Issue: 623(7985), P. 77 - 82

Published: Nov. 1, 2023

Language: Английский

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Palladium Hydride-Enabled Hydroalkenylation of Strained Molecules

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(45), P. 20875 - 20883

Published: Oct. 31, 2022

We report the first palladium hydride enabled hydroalkenylation of strained molecules. This new mild protocol proceeds via a regio- and chemoselective hydropalladation step, followed by photoinduced radical alkyl Heck reaction. methodology represents reactivity mode for molecules opens avenues catalysis. The reaction is compatible with wide range functional groups can be applied to complex structures, delivering diverse array highly valuable modifiable alkenylated cyclobutanes cyclopropanes. A hydroalkenylation/diastereoselective rearrangement cascade toward cyclopentene scaffold has also been demonstrated.

Language: Английский

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Anaerobic Hydroxylation of C(sp³)–H Bonds Enabled by the Synergistic Nature of Photoexcited Nitroarenes

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(5), P. 2794 - 2799

Published: Jan. 25, 2023

A photoexcited-nitroarene-mediated anaerobic C-H hydroxylation of aliphatic systems is reported. The success this reaction due to the bifunctional nature photoexcited nitroarene, which serves as bond activator and oxygen atom source. Compared previous methods, approach cost- atom-economical commercial availability sole mediator reaction. Because conditions transformation, a noteworthy expansion in substrate scope can be obtained compared prior reports. Mechanistic studies support that nitroarenes engage successive hydrogen transfer radical recombination events with hydrocarbons, leading N-arylhydroxylamine ether intermediates. Spontaneous fragmentation these intermediates leads key products.

Language: Английский

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Carbon–Carbon Bond Cleavage for Late-Stage Functionalization

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(22), P. 12313 - 12370

Published: Nov. 9, 2023

Late-stage functionalization (LSF) introduces functional group or structural modification at the final stage of synthesis natural products, drugs, and complex compounds. It is anticipated that late-stage would improve drug discovery's effectiveness efficiency hasten creation various chemical libraries. Consequently, products a productive technique to produce product derivatives, which significantly impacts biology development. Carbon-carbon bonds make up fundamental framework organic molecules. Compared with carbon-carbon bond construction, activation can directly enable molecular editing (deletion, insertion, atoms groups atoms) provide more efficient accurate synthetic strategy. However, selective unstrained still one most challenging projects in synthesis. This review encompasses strategies employed recent years for cleavage by explicitly focusing on their applicability functionalization. expands current discourse reactions providing comprehensive overview types bonds. includes C-C(sp), C-C(sp2), C-C(sp3) single bonds; double triple bonds, focus catalysis transition metals organocatalysts. Additionally, specific topics, such as ring-opening processes involving three-, four-, five-, six-membered rings, are discussed, exemplar applications these techniques showcased context bioactive molecules discovery. aims shed light advancements field propose potential avenues future research realm

Language: Английский

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Light-promoted aromatic denitrative chlorination

Nature Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 20, 2025

Language: Английский

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Nitroarenes: The rediscovery of their photochemistry opens new avenues in organic synthesis

Chem, Journal Year: 2023, Volume and Issue: 9(12), P. 3401 - 3414

Published: Nov. 14, 2023

Language: Английский

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Photocatalyzed Oxygenation Reactions with Organic Dyes: State of the Art and Future Perspectives

Catalysts, Journal Year: 2023, Volume and Issue: 13(2), P. 220 - 220

Published: Jan. 18, 2023

Oxygen atom incorporation into organic molecules is one of the most powerful strategies to increase their pharmacological activity and obtain valuable intermediates in synthesis. Traditional oxidizing agents perform very well, but environmental impact low selectivity constitute significant limitations. On contrary, visible-light-promoted oxygenations represent a sustainable method for compounds, since only molecular oxygen photocatalyst are required. Therefore, photocatalytic oxygenation reactions exhibit high atom-economy eco-compatibility. This mini-review collects analyzes recent literature on organo-photocatalysis applications promote selective substrates. In particular, acridinium salts, Eosin Y, Rose Bengal, cyano-arenes, flavinium quinone-based dyes widely used as photocatalysts several transformations alkanes, alkenes, alkynes, aromatic amines, phosphines, silanes, thioethers. this context, organo-photocatalysts proved be highly efficient catalytic terms, showing similar or even superior performances with respect metal-based counterparts, while maintaining impact. addition, given mild reaction conditions, photo-oxygenation processes often display remarkable selectivity, which striking feature late-stage functionalization complex molecules.

Language: Английский

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Photocatalytic carboxylation of styrenes with CO2 via C=C double bond cleavage

CHINESE JOURNAL OF CATALYSIS (CHINESE VERSION), Journal Year: 2024, Volume and Issue: 56, P. 74 - 80

Published: Jan. 1, 2024

Language: Английский

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Aziridination via Nitrogen-Atom Transfer to Olefins from Photoexcited Azoxy-Triazenes

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(14), P. 9499 - 9505

Published: March 24, 2024

Herein, we report that readily accessible azoxy-triazenes can serve as nitrogen atom sources under visible light excitation for the phthalimido-protected aziridination of alkenes. This approach eliminates need external oxidants, precious transition metals, and photocatalysts, marking a departure from conventional methods. The versatility this transformation extends to selective both activated unactivated multisubstituted alkenes varying electronic profiles. Notably, process avoids formation competing C–H insertion products. described protocol is operationally simple, scalable, adaptable photoflow conditions. Mechanistic studies support idea photofragmentation results in generation free singlet nitrene. Furthermore, mild photoredox-catalyzed N–N cleavage protecting group furnish aziridines reported. Our findings contribute advancement sustainable practical methodologies synthesis nitrogen-containing compounds, showcasing potential broader applications synthetic chemistry.

Language: Английский

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Visible photons as ideal reagents for the activation of coloured organic compounds

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

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