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Article
Chemistry, Organic
Hai-Yang Song et al.
Summary: A simple and practical electron donor-acceptor (EDA) strategy is reported for synthesizing various 3-alkylated coumarins from easily available coumarins and naturally abundant carboxylic acids under photocatalyst-, oxidant-, and additive-free and mild conditions. By using Na2S as the catalytic electron donor, a series of primary, secondary, and tertiary carbon radicals can be efficiently generated, and the EDA complex can be regenerated without the need for an alkaline additive.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hai-Yang Song et al.
Summary: We developed a novel and efficient method for the synthesis of various 3-alkylated quinoxalin-2(1H)-ones through an electron donor-acceptor complex enabled alkylation. This method utilized N-hydroxyphthalimide esters as the alkyl source and Na2S as the catalytic electron donor, achieving high yields (70%-96%) under photocatalyst-, oxidant-, and additive-free conditions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Haidi Tang et al.
Summary: Researchers have developed a method for synthesizing thioesters through carbonyl thiyl radical-based reactions, using direct photocatalyzed hydrogen atom transfer. This method allows for the synthesis of complex pharmaceutical molecules from readily available commodity chemicals. The study provides a new approach for the application of thiol-ene click chemistry in organic synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Applied
He-Yang Zhou et al.
Summary: The electrostatic attraction between electrons and nuclei is a fundamental force in electrochemistry, driving the interaction between them and enabling redox reactions. Recent advancements in organic electrochemistry have focused on optimizing electrode materials, developing new catalysts, and exploring interdisciplinary combinations to enhance reaction mechanisms. These developments have contributed to the efficient and environmentally friendly creation of reactive intermediates.
CHINESE JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Hai-Yang Song et al.
Summary: This study reports the use of a semi-heterogeneous g-C3N4/NaI dual catalytic system for the C-C bond formation between quinoxalin-2(1H)-ones and arylhydrazines under blue light irradiation. The photo-generated hole acts as a traceless oxidant, facilitating the redox catalyst cycle of the iodide salt, while the photo-generated electron serves as a clean reductant, promoting the bond formation process. A wide range of 3-arylquinoxaline-2(1H)-ones were obtained with high yields and excellent functional group tolerance.
Article
Chemistry, Applied
Qing-Wen Gui et al.
Summary: The Z-scheme V2O5/g-C3N4 heterojunction was employed in a heterogeneous visible light-induced cascade reaction to synthesize phosphorylated ring-fused quinazolinones. Both the photogenerated hole and photogenerated electron played a crucial role in the radical cascade process.
CHINESE JOURNAL OF CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Natalie Holmberg-Douglas et al.
Summary: The fields of C-H functionalization and photoredox catalysis have gained significant interest and utility in various scientific disciplines. This review focuses on the use of photoredox catalysis in C-H functionalization reactions, highlighting both inorganic/organometallic and organic-based photoredox catalytic systems. The subdivision by reaction class (sp(2) or sp(3) C-H functionalization) provides perspective and tactical strategies for synthetic applications.
Review
Chemistry, Multidisciplinary
Fan Gao et al.
Summary: This minireview gives an overview of the progress on the application of graphene oxide (GO) as a catalyst for various organic transformations in the past decade.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Anzai Shi et al.
Summary: A sustainable and cost-effective method for the synthesis of imidazolidine-fused sulfamidates using CsPbBr3 as a heterogeneous photocatalyst has been developed. The catalyst can be easily recovered and reused at least five times without a significant decrease in its photocatalytic reactivity, demonstrating a high catalyst economic feature.
Article
Chemistry, Multidisciplinary
Zhiwei Wang et al.
Summary: A mild and efficient photochemical multi-component tandem reaction for the synthesis of sulfonated quinoxalin-2(1H)-ones is reported. The reaction can be carried out at room temperature using metal-free photocatalyst 4CzIPN and environmentally benign oxidant dioxygen. The reaction exhibits good functional group tolerance and the radical reaction mechanism is elucidated through experiments.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Zhi-Lin Wu et al.
Summary: A novel and efficient electro-chemical initiated radical strategy was developed for the preparation of both N-substituted and N-unsubstituted 4-selanylisoquinolin-1(2H)-ones through selenylation of isoquinolin-1(2H)-ones with organodiselenides under chemical oxidant-, additive-free and ambient conditions.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Panjie Xiang et al.
Summary: An S(N)2-based photochemical strategy using dithiocarbamate anion as catalyst has been developed for the activation of benzyl halides, allowing the benzylation (or cyanomethylation) of various heterocycles with high yields. This transition-metal-free and oxidant-free protocol also enables the synthesis of biologically relevant compounds under mild conditions.
CHINESE CHEMICAL LETTERS
(2022)
Review
Chemistry, Multidisciplinary
Daoshan Yang et al.
Summary: This review focuses on recent advances in C-S bond formation via visible-light photoredox catalysis, highlighting its potential in pharmaceutical synthesis, synthetic methodology development, and the application of sulfur-containing drugs.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Yueyue Zhu et al.
Summary: In this study, a novel and efficient synthetic method was developed to construct isoquinolone scaffold and other valuable derivatives through catalytic reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Ban Wang et al.
Summary: Readily available and facilely tunable pyridine N-oxides have been developed as effective photoinduced hydrogen-atom-transfer (HAT) catalysts for site-selective C-H functionalizations. The pyridine N-oxide radicals generated from Noxides by photoredox catalyzed single-electron oxidation are the key intermediates for achieving alkylation, amination, azidation, allylation, and cyanation. The fine-tuning of reactivity and selectivity through operational simple structural modification shows promising capability for selective functionalization of unactivated C(sp(3))-H bonds.
Article
Chemistry, Physical
Anzai Shi et al.
Summary: The oxygen-doped graphite-like carbon nitride (OCN) photocatalyst shows better catalytic performance under visible light irradiation compared to the original, offering a potential expansion in the development of novel heterogeneous photocatalysts for applications in organic synthesis.
JOURNAL OF CATALYSIS
(2022)
Review
Chemistry, Organic
Xu Hao et al.
Summary: This paper summarizes the recent advances of different sulfonium salts in radical type reactions induced by visible light, including the formation reactions of C-C and C-X bonds, and discusses the applicable scope and mechanism of some reactions.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Li Hongxia et al.
Summary: A practical method for the synthesis of various thiocyanated 5-membered aromatic heterocycles through electrochemical cross-coupling of heterocycles (pyrazoles, pyrroles, furans and thiophenes) with NH4SCN under chemical oxidant-and exogenous electrolyte-free conditions was developed.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hai-Xia Wang et al.
Summary: An electrosynthetic approach for the oxidative C-H/N-H cross-coupling amination of cyclic sulfamidate imines was developed. This method offers high functional group compatibility and can be easily scaled up. It provides an efficient tool with broad potential application prospects in medicinal and synthesis chemistry.
Article
Chemistry, Multidisciplinary
Lukasz W. Ciszewski et al.
Summary: Pyridine N-oxides have been recently discovered as effective reagents in the photocatalysis field, serving as precursors for oxypyridinium salts and hydrogen atom transfer in alkylation reactions of electron-deficient heteroarenes. This method eliminates the need for a photocatalyst and allows for efficient alkylation of a broad range of azines using various radical precursors.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Elpida Skolia et al.
Summary: In this study, a novel and sustainable light-driven method for synthesizing sulfoxides was developed and the impact of different wavelength irradiation on sulfide oxidation was investigated.
Article
Chemistry, Organic
Wang Feng et al.
Summary: The allylation of benzol[e][1,2,3]oxathiazine-2,2-dioxides with allyl bromides promoted by tin powder was investigated. The reaction proceeded smoothly with high yields for various substrates. The resulting allylated products underwent N-allylation reaction and then ring closing metathesis reaction, leading to the formation of diallylated products and cyclic derivatives of benzol[e][1,2,3]oxathiazine-2,2-dioxides, respectively.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiaotong Wang et al.
Summary: A visible-light-induced metal-free cascade cyclization was developed for the synthesis of N-sulfonamide-fused imidazolidines. The reaction used 3 mol% of eosin Y as the photocatalyst at room temperature under visible light irradiation, resulting in good yields of the desired products (32 examples, up to 86% yields).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiao-Ya Yuan et al.
Summary: The direct coupling reaction between inert alkanes and quinoxalin-2(1H)-ones was successfully achieved under noble metal-free, acid-free, and oxidant-free conditions, leading to the synthesis of various 3-alkylated quinoxalin-2(1H)-ones with good to excellent yields.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Min Wang et al.
Summary: A direct and convenient strategy for the synthesis of 3-alkylquinoxalin-2(1H)-ones and other alkyl N-heteroarenes has been developed. This strategy involves a photocatalyzed alkylation of quinoxalin-2(1H)-ones and other N-heterocycles using commercially available, low-cost alkanes under ambient conditions, with phenanthrenequinone as the photocatalyst. The transformation offers advantages of an environment-friendly protocol, mild conditions, good functional-group tolerance, and high yields of products.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Applied
Shaonan Zhang et al.
Summary: We report a convenient and economic approach for the site-selective C(sp(3))-H sulfonylation of hydrocarbons via photo-induced hydrogen atom transfer (HAT) catalysis. This method converts toluene derivatives and cycloalkanes into biologically and synthetically interesting sulfone products, offering an opportunity to obtain high value-added products from abundant hydrocarbon starting materials and inexpensive reagents.
CHINESE JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Qing-Wen Gui et al.
Summary: An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles has been developed through a visible-light induced one-pot tandem reaction. The reaction proceeded without the need for any additive, base, metal-catalyst, or external photosensitizer, using cheap reagents and biomass-derived solvent. Successful difluoromethylation of N-arylacrylamide substrates was achieved in good to excellent yields.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Jun Xu et al.
Summary: A Minisci-type cross-dehydrogenative alkylation was reported using cerium chloride as a photocatalyst and air as an oxidant, showing excellent tolerance to functional groups and suitability for both heteroarene and alkane substrates, providing an alternative approach for late-stage functionalization of valuable substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Jun Jiang et al.
Summary: Clean production, as an important part of green chemistry, has received great attention and considerable development in recent years. Using eco-friendly solvents, (nearly) quantitative synthesis, clean separation, and purification can be achieved to obtain pure products easily.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Jingjing Wang et al.
Summary: The silver-catalyzed decarboxylative C-H alkylation of cyclic aldimines with abundant aliphatic carboxylic acids has been achieved under mild reaction conditions, producing moderate to good yields (32%-91%). The study also demonstrated the potential of the technology in gram-scale reactions and late-stage modification of drugs.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Organic
Zhen-Yao Dai et al.
Summary: The asymmetric functionalization of inert C(sp(3))-H bonds was achieved using a photocatalytic method with TBADT and chiral phosphoric acid, allowing rapid synthesis of enantioenriched astereogenic esters from simple raw materials.
Article
Chemistry, Multidisciplinary
Lingling Yao et al.
Summary: This study developed a visible-light-induced chemoselective reaction of quinoxalin-2(1H)-ones with alkylboronic acids, providing different products. The strategy accommodates a broad scope of substituted quinoxalin-2(1H)-ones and alkylboronic acids with good product yields.
CHINESE CHEMICAL LETTERS
(2021)
Review
Chemistry, Multidisciplinary
Homa Targhan et al.
Summary: Hydrogen peroxide can serve as an indispensable oxidizing agent in organic reactions, showcasing its satisfactory performance in terms of economy, technology, and environment in various reactions.
JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY
(2021)
Article
Chemistry, Organic
Sukanya Neogi et al.
Summary: A mild, efficient, and one-pot protocol for three-component carbosilylation of alkenes with imidazoheterocycle and silanes has been developed by merging iron(II) and visible-light photocatalysis. This C-C and C-Si bond-forming method provides functionalized organosilicon derivatives having imidazoheterocycles moieties in good yields. The reaction possibly proceeds through a radical pathway.
Article
Chemistry, Multidisciplinary
Yongqiang Zhang et al.
Summary: The visible light-induced metal-free C(sp(3))-H phenanthridinylation of simple alkanes with isonitrile using H2O2 as a terminal green oxidant enables practical access to valuable alkyl-substituted phenanthridine derivatives with good yields and selectivities under mild conditions and broad substrate scope, including gaseous alkanes.
Review
Chemistry, Multidisciplinary
Soumitra Guin et al.
Summary: The chemistry of cyclic N-sulfonyl ketimines and their derivatives has attracted attention due to their intriguing structures and properties. These compounds serve as reactive synthons in various reactions and can create a diverse set of synthetically and biologically attractive molecules. Chemists focus on manipulating the highly reactive C=N bond of N-sulfonyl ketimines in synthetic reactions to form a wide range of fascinating compounds.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Jonathan D. Bell et al.
Summary: This review explores the progress of photoredox chemistry with organic or transition metal agents, focusing on recent examples of bond formations using radical intermediates. The emphasis is on developments in the past 10 years, highlighting advances in transition metal and organic photoredox reagents chemistry.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Dawei Cao et al.
Summary: A simple and efficient method for cross-coupling of aryl halides with different alkyl disulfides was developed under mild conditions. The reaction proceeded without the need for transition metal or external photosensitizer under air, and resulted in excellent yields with a broad substrate scope tolerant of various functional groups.
GREEN SYNTHESIS AND CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Yunhe Jin et al.
Summary: The iron-catalysed photoredox system reported in this study enables the transformation of light alkanes into C-N and C-C bonds under ambient temperature, demonstrating high catalytic efficiency, mild conditions, and convenience in purification and scaling up. The system is sustainable, convenient, and environmentally friendly, with potential applications in high-value-added transformations of natural alkanes.
Article
Chemistry, Applied
Igor B. Krylov et al.
Summary: The study demonstrates a new type of mixed heterogeneous/homogeneous catalysis for selective alkylarene oxidation by utilizing the interaction between NHPI and TiO2, leading to an increase in energy efficiency.
CHINESE JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Organic
Xue Liu et al.
Summary: This methodology enables the streamline assembly of amine derivatives via radical mediated C-N bond formation under transition-metal-free conditions, with good functional group tolerance and yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jingjing Wang et al.
Summary: This study describes a silver-catalyzed approach for direct C-H functionalization of cyclic aldimines with cyclopropanols and cyclobutanols via a radical-mediated C-C bond cleavage strategy. The desired products were obtained in decent yields with a wide substrate scope under mild reaction conditions. Furthermore, gram-scale reaction and synthetic transformation of the product were successfully conducted.
CHEMICAL COMMUNICATIONS
(2021)
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Pin Xu et al.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES
(2013)
Review
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Spencer J. Williams
EXPERT OPINION ON THERAPEUTIC PATENTS
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(2010)