Visible light-induced organophotoredox-catalyzed difunctionalization of alkenes and alkynes

Green Chemistry, Год журнала: 2023, Номер 25(21), С. 8459 - 8493

Опубликована: Янв. 1, 2023

This review comprehensively summarizes visible light-induced difunctionalization strategies for alkene and alkyne systems in metal-free conditions with literature coverage up to July 2023.

Язык: Английский

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CsPbBr₃-Modified Oxygen-Doped g-C₃N₄ Heterojunctions for Sulfurization of Alkenes to Sulfoxides

Inorganic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 3, 2025

Z-scheme heterostructures have become a novel class of photocatalysts that hold substantial significance in the domains environmental and energy-related applications. This can be attributed to their distinctive charge separation transfer pathways, which endow heterojunctions with robust redox capabilities. In this paper, we report straightforward method for fabricating perovskite-based heterojunction by integrating CsPbBr3 nanocrystals oxygen-doped g-C3N4 (OCN). exhibited high photocatalytic activity selective sulfoxidation reaction alkenes thiols. Under aerobic conditions, moderate excellent yields high-value sulfoxides good functional compatibilities were achieved. showcases outstanding performance, remarkable stability, operational simplicity, atom efficiency, eco-friendly energy sources. The formation was corroborated situ X-ray photoelectron spectroscopy. These spectra revealed negative shift binding energies Cs 1s, Pb 4f, Br 3d CsPbBr3, while positive observed C N O 1s OCN upon light irradiation. specific pattern effectively promotes electron from is conducive electrons holes, thereby enhancing photoredox catalytic activity.

Язык: Английский

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Metal‐Free Visible‐light Mediated C−S Bond Formation

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(8)

Опубликована: Июнь 26, 2023

Abstract The upsurge in interest the development of methodologies for synthesis sulfur‐containing compounds via use visible‐light has been established as a sustainable tool organic chemistry. Particularly, mediated C−S bond formation gained popularity due to its operational simplicity, minimized by‐products, easy handling, mild reaction conditions, etc. Photochemistry not only provides way synthesize complex molecules but also ability overcome many challenges which are difficult attain by conventional thermal pathways. Owing biological importance compounds, present review focused on under metal‐free conditions visible‐light. objective current is bring out unearthing collection regarding photoredox catalysis. For better understanding, categorized according mode reactions viz , difunctionalization alkenes and alkynes, C−H functionalization, radical cyclization. All each sections described with selected examples proper explanation proposed mechanism.

Язык: Английский

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Organophotoredox Catalysis: Switchable Radical Generation from Alkyl Sodium Sulfinates for Sulfonylation and Alkylative Activation of C–C Bonds of Cyclopropenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(6), С. 3912 - 3925

Опубликована: Март 6, 2024

Generating alkyl radicals from the sulfonyl remains challenging in synthetic chemistry. Here, we report an efficient photocatalyzed strategy using sodium sulfinates as both sulfonylating and alkylating reagents by controlling reaction temperature. This methodology provides a versatile protocol for synthesizing diastereoselective sulfonylated cyclopropanes poly-substituted styrene derivatives. is successfully demonstrated with wide variety of cyclopropenes sulfinates, showcasing its broad substrate scope, high diastereo- E/Z selectivity, yielding good to excellent yields.

Язык: Английский

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Progress on direct transformation of thiols to sulfinyl compounds

Phosphorus, sulfur, and silicon and the related elements, Год журнала: 2025, Номер unknown, С. 1 - 9

Опубликована: Янв. 26, 2025

Язык: Английский

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Photoinduced Cerium‐Mediated Decarboxylative Alkylation Cascade Cyclization of N‐arylacrylamides and N‐acryl‐2‐aryl benzimidazoles

Chemistry - An Asian Journal, Год журнала: 2023, Номер 18(8)

Опубликована: Фев. 28, 2023

Abstract A mild and versatile cerium‐mediated decarboxylative strategy for sequential alkylation/cyclization was developed the synthesis of quaternary oxindoles benzimidazo[2,1‐ a ]isoquinolin‐6(5 H )‐ones via photoinduced‐LMCT. This operationally simple procedure relies on inexpensive feedstock carboxylic acids as alkyl radical surrogates aerial molecular oxygen terminal oxidant. atom economical protocol showed viability with wide range (1° to 3° acids) coupling partners also allows late‐stage modification pharmaceutically‐important acids. Mechanistic studies revealed reaction follow pathway, while event studied by in situ FTIR.

Язык: Английский

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Cu^I-Catalyzed Radical Reaction of Benzimidates to Form Valuable 4,5-Dihydrooxazoles through Regioselective Aerobic Oxidative Cross-Coupling

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(4), С. 2703 - 2717

Опубликована: Янв. 31, 2024

A straightforward Cu(I)-catalyzed oxidative cross-coupled organic transformation has been developed under mild conditions for the construction of functionalized 4,5-dihydrooxazoles through a four-bond-forming regiocontrolled C–C/C–N/C–O coupling strategy emerging benzimidates, paraformaldehyde, and 1,3-diketo analogues using eco-friendly O2 as sole oxidant. The fundamental features these designed approaches involve operational simplicity, selectivity, generality, broad substrate scope with high yields same reaction conditions.

Язык: Английский

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Nanomole‐scale photochemical thiol‐ene chemistry for high‐throughput late‐stage diversification of peptide macrocycles

Peptide Science, Год журнала: 2023, Номер 116(1)

Опубликована: Апрель 26, 2023

Abstract The photochemical thiol‐ene reaction is an efficient method for rapid and chemoselective formation of thioether linkages under mild conditions. It has found widespread use in small‐molecule synthesis as well peptide protein chemistry. While high‐throughput experimentation provides invaluable tool drug discovery, the considerable potential remains unexplored this context. Herein, we report development nanomole‐scale chemistry, performed using automated approach 1536‐well plates a cost‐efficient custom reactor. Through careful design selection reactants, chemistry applied to lateral diversification peptidic macrocycles yield high purity crude mixtures. Selection photoinitiator 2,2‐dimethoxy‐2‐phenylacetophenone yields volatile breakdown products, which facilitates removal vacuo. We demonstrate late‐stage with 96 examples averaging 95% conversion desired product.

Язык: Английский

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Selective Syntheses of Unsymmetrical Diaryl Sulfides Enabled by a Sulfur Dioxide Surrogate as a Divalent Sulfur Source and an Activating Agent

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 15348 - 15355

Опубликована: Окт. 2, 2024

Язык: Английский

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Cu(I)-Catalyzed C(sp³)–H Functionalization of Amino Acids with Benzimidate and Reactive Oxygen Species (ROS) To Synthesize Triazines and 2-Pyrrolidinones

Organic Letters, Год журнала: 2024, Номер 26(46), С. 9828 - 9834

Опубликована: Ноя. 11, 2024

An easily accessible Cu(I)-catalyzed regioselective oxidative C-N/C-O cross-coupling organic transformation has been disclosed for the syntheses of variably functionalized triazines and N-benzoylpyrrolidin-2-ones through involvement C(sp

Язык: Английский

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