4.7 Article

Visible-light-mediated multi-component carbene transfer reactions of α-diazoesters to construct multisubstituted pyrazoles and 1,3-dicarbonyl derivatives

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

DMSO as a C1 Source for [2+2+1] Pyrazole Ring Construction via Metal-Free Annulation with Enaminones and Hydrazines

Haijin Guo et al.

Summary: The synthesis of 1,4-disubstituted pyrazoles was successfully achieved through a cascade reaction between enaminones, hydrazines, and DMSO catalyzed by molecular iodine in the presence of Selectfluor. DMSO played a dual role as the C-1 source and the reaction medium, and the synthesis of 1,3,4-trisubstituted pyrazoles using aldehydes as alternative C-1 building blocks was also accomplished.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

Visible-Light-Promoted Aerobic Oxyphosphorylation of α-Diazoesters with H-Phosphine Oxides

Hongyan Zhou et al.

Summary: In this study, a visible-light-promoted aerobic oxyphosphorylation of alpha-diazoesters and H-phosphine oxides has been developed. The reaction proceeds smoothly at room temperature using air as the oxygen source and blue-light irradiation. Preliminary mechanistic studies indicate the involvement of a light-triggered radical process. This strategy reveals the previously unknown reactivity of diazo compounds with H-phosphine oxides and has potential value in synthetic applications.

ORGANIC LETTERS (2022)

Article Chemistry, Organic

A visible light-mediated three-component strategy based on the ring-opening of cyclic ethers with aryldiazoacetates and nucleophiles

Mateus L. Stivanin et al.

Summary: A blue light-promoted reaction has been developed, which allows the incorporation of aryldiazoacetates and different nucleophiles into a single product using THF (and other cyclic ethers) as the solvent. This transformation represents an O-H insertion strategy of complex alcohols into aryldiazoesters without pre-assembling. The method is mild and efficient, and can proceed at room temperature without the need for metals.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Organic

Carbene-enabled ether activation through the formation of oxonium: a theoretical view

Ya-Nan Wang et al.

Summary: Theoretical investigation of carbene-enabled ether activation revealed that the final products were dependent on the stability of the oxonium intermediate, achieved through nucleophilic attack of ethers onto carbene species. The nucleophilicity of ethers was found to be crucial for polarization and charge transfer, influencing the chemoselectivity of the reaction. Surprisingly, solvation of ethers did not play a significant role in determining the outcome of the reaction.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

Visible-light-initiated 4CzIPN catalyzed multi-component tandem reactions to assemble sulfonated quinoxalin-2(1H)-ones

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

Visible-light-driven multicomponent reactions to access S-alkyl phosphorothioates using elemental sulfur as the sulfur source

Chengming Qu et al.

Summary: A metal-free strategy using visible-light-driven four-component reactions has been developed to construct S-alkyl phosphorothioates. This method utilizes DBU as an additive and elemental sulfur as a cheap and odorless sulfur source, providing an efficient approach to access various S-alkyl phosphorothioates under mild conditions. Additionally, three-component coupling products can be obtained conveniently by changing the reaction solvent.

GREEN CHEMISTRY (2022)

Article Chemistry, Organic

Elemental sulfur as the S source: visible-light-mediated four-component reactions leading to thiocyanates

Zhiwei Wang et al.

Summary: This research presents an eco-friendly and photocatalyst-free four-component reaction that is promoted by visible light. By using odorless elemental sulfur as the S source, a series of diverse organic thiocyanates were obtained conveniently at room temperature. This method avoids the use of metal reagents, strong oxidants, awful smelling materials, and harsh reaction conditions.

ORGANIC CHEMISTRY FRONTIERS (2022)

Article Chemistry, Multidisciplinary

Visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na leading to 3-trifluoroalkylated quinoxalin-2(1H)-ones

Na Meng et al.

Summary: A metal-free visible-light-enabled three-component reaction has been developed, which utilizes quinoxalin-2(1H)-ones, alkenes, and CF3SO2Na under air at room temperature. This photocatalytic tandem reaction using 4CzIPN as the photocatalyst and air as the green oxidant provides a mild and environmentally friendly approach to access a series of 3-trifluoroalkylated quinoxalin-2(1H)-ones.

CHINESE CHEMICAL LETTERS (2021)

Article Chemistry, Organic

Visible-Light-Promoted Polysubstituted Olefins Synthesis Involving Sulfur Ylides as Carbene Trapping Reagents

Cong Ye et al.

Summary: The method uses a blue-light LED to promote the coupling of aryl diazoacetates with sulfur ylides, featuring mild conditions, good functional group tolerance, and a broad substrate scope. Under optimal reaction conditions, a variety of trisubstituted olefins can be synthesized and further transformed into other important biologically active heterocycles.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

DMSO as a Methine Source in TFA-Mediated One-Pot Tandem Regioselective Synthesis of 3-Substituted-1-Aryl-1H-Pyrazolo-[3,4-b]quinolines from Anilines and Pyrazolones

Pushpendra Yadav et al.

Summary: An acid-mediated and DMSO participant one-pot tandem synthesis of 3-substituted-1-aryl-1H-pyrazolo-[3,4-b]quinoline has been achieved from readily available anilines and pyrazolones. This environmentally benign approach enables regioselective construction of valuable heterocycles without the need for transition metals and oxidants. A variety of substituted aryl amines and pyrazolines can be successfully employed in this reaction, accessing a range of pyrazolo[4,3-c]quinolones through a novel cascade mechanism. Additionally, the application and mechanistic studies of this methodology have been demonstrated.

JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates: An approach to 2,3-dihydrobenzofuran derivatives

Shuangjing Zhou et al.

Summary: A visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates has been developed, providing a mild and efficient approach for the synthesis of biologically important 2,3-dihydrobenzofuran derivatives in good yields and moderate diastereoselectivities.

CHINESE CHEMICAL LETTERS (2021)

Article Chemistry, Organic

Oxime Ether Synthesis through O-H Functionalization of Oximes with Diazo Esters under Blue LED Irradiation

Qian Li et al.

Summary: A green and sustainable oxime ether formation method using visible light to promote the O-H functionalization of oximes with diazo esters is efficient and versatile, with high yields and tolerance to various functional groups. When a cyclic ether solvent is used, such as THF, 1,4-dioxane, and tetrahydropyran, an interesting photochemical three-component reaction product can be obtained in good yields.

ORGANIC LETTERS (2021)

Article Chemistry, Multidisciplinary

Lightening Diazo Compounds?

Jakub Durka et al.

Summary: Diazo compounds are valuable reagents in organic synthesis, and their photochemical reactions under visible light irradiation offer sustainable and efficient alternatives to transition metal catalysis. These reactions have shown promising applications in various transformations, highlighting a potential future direction for greener synthetic methodologies.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2021)

Review Chemistry, Organic

Study on the Application of Photoelectric Technology in Synthesis of Selenium-Containing Heterocycles

Wang Xin et al.

Summary: This paper describes the synthesis reactions of selenium-containing heterocycles, mainly driven by electrochemical and visible light technologies, expanding the application prospects in various fields, and discusses the applicable scope and mechanism of some reactions.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Visible Light Induced Oxidation of a-Diazo Esters for the Transition Metal-Free Synthesis of a-Keto Esters

Zhao Baoli et al.

Summary: An aerobic oxidation approach using oxygen as an oxidant for the synthesis of a-keto esters has been developed. The transformation is achieved by inducing visible light with eosin Y, allowing reactions to proceed at room temperature under air atmosphere with broad substrate tolerance. This provides a green and facile synthetic approach for structurally diverse a-keto esters.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Organic

Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate

Cai Baogui et al.

Summary: The visible light-promoted transformation of diazo compounds through the formation of free carbene is a significant advancement in organic synthesis, aligning with the principles of green chemistry. Chinese research groups have made noteworthy contributions to this field, which is expected to continue to grow and face new challenges in the future.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

Article Chemistry, Organic

Metal-free visible-light-induced aerobic oxidation of α-diazoesters leading to α-ketoesters in air

Ruisheng Liu et al.

Summary: A metal-free, visible-light-promoted strategy has been developed for the construction of alpha-ketoesters via aerobic oxidation of alpha-diazoesters with dioxygen at room temperature. Using cheap Eosin Y as the photocatalyst and O-2(air) as the oxidant, this protocol offers a mild and efficient approach to a wide range of alpha-ketoesters in moderate to good yields. Preliminary mechanistic studies indicate the involvement of photo-excited singlet oxygen in the reaction system.

ORGANIC CHEMISTRY FRONTIERS (2021)

Article Chemistry, Multidisciplinary

Electrochemical multicomponent synthesis of 4-selanylpyrazoles under catalyst- and chemical-oxidant-free conditions

Yan Wu et al.

Summary: An electrochemical multicomponent reaction was developed for the construction of 4-selanylpyrazoles under catalyst- and chemical-oxidant-free conditions, providing a green and straightforward protocol. A variety of 4-selanylpyrazole derivatives were synthesized from readily available raw materials with good to excellent yields.

GREEN CHEMISTRY (2021)

Article Chemistry, Organic

Synthesis of trisubstituted hydroxylamines by a visible light-promoted multicomponent reaction

Bao-Gui Cai et al.

Summary: An efficient method for synthesizing trisubstituted hydroxylamines has been developed using beta-keto ester, 2-nitrosopyridine, and aryldiazoacetates. This multicomponent reaction can easily produce two different kinds of trisubstituted hydroxylamines by simply changing the reaction media.

ORGANIC CHEMISTRY FRONTIERS (2021)

Review Chemistry, Multidisciplinary

Visible light-promoted ring-opening functionalization of three-membered carbo- and heterocycles

Jun Xuan et al.

CHEMICAL SOCIETY REVIEWS (2020)

Article Chemistry, Organic

Copper-Catalyzed Aminoboration from Hydrazones To Generate Borylated Pyrazoles

Kim N. Tu et al.

ORGANIC LETTERS (2019)

Article Chemistry, Multidisciplinary

Blue-Light-Induced Carbene-Transfer Reactions of Diazoalkanes

Rene Hommelsheim et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

Review Chemistry, Organic

Recent developments in photochemical reactions of diazo compounds

Lukasz W. Ciszewski et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

Article Chemistry, Multidisciplinary

Visible light mediated, metal-free carbene transfer reactions of diazoalkanes with propargylic alcohols

Feifei He et al.

CHEMICAL COMMUNICATIONS (2019)

Article Chemistry, Multidisciplinary

Photochemical ring expansion reactions: synthesis of tetrahydrofuran derivatives and mechanism studies

Sripati Jana et al.

CHEMICAL SCIENCE (2019)

Article Chemistry, Multidisciplinary

Blue light-promoted cross-coupling of aryldiazoacetates and diazocarbonyl compounds

Tiebo Xiao et al.

CHEMICAL COMMUNICATIONS (2018)

Article Chemistry, Multidisciplinary

Blue light-promoted photolysis of aryldiazoacetates

Igor D. Jurberg et al.

CHEMICAL SCIENCE (2018)

Review Chemistry, Medicinal

Recent advances of pyrazole-containing derivatives as anti-tubercular agents

Zhi Xu et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2017)

Article Chemistry, Organic

Asymmetric Synthesis of Amino-Bis-Pyrazolone Derivatives via an Organocatalytic Mannich Reaction

Pankaj Chauhan et al.

JOURNAL OF ORGANIC CHEMISTRY (2017)

Review Chemistry, Multidisciplinary

Visible light photoredox-controlled reactions of N-radicals and radical ions

Jia-Rong Chen et al.

CHEMICAL SOCIETY REVIEWS (2016)

Review Chemistry, Medicinal

The therapeutic voyage of pyrazole and its analogs: A review

Mohemmed Faraz Khan et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2016)

Article Chemistry, Multidisciplinary

Asymmetric synthesis of pyrazoles and pyrazolones employing the reactivity of pyrazolin-5-one derivatives

Pankaj Chauhan et al.

CHEMICAL COMMUNICATIONS (2015)

Article Chemistry, Multidisciplinary

p-Toluenesulphonic acid-promoted, I-2-catalysed sulphenylation of pyrazolones with aryl sulphonyl hydrazides

Xia Zhao et al.

CHEMICAL COMMUNICATIONS (2014)

Review Chemistry, Multidisciplinary

Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis

Christopher K. Prier et al.

CHEMICAL REVIEWS (2013)

Review Chemistry, Medicinal

Pyrazole containing natural products: Synthetic preview and biological significance

Vinod Kumar et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2013)

Article Chemistry, Organic

Chemistry of Pyrazolinones and their Applications

Wafaa S. Hamama et al.

CURRENT ORGANIC CHEMISTRY (2012)

Review Chemistry, Multidisciplinary

From 2000 to Mid-2010: A Fruitful Decade for the Synthesis of Pyrazoles

Santos Fustero et al.

CHEMICAL REVIEWS (2011)

Article Chemistry, Organic

Recent Advances in the Chemistry of Pyrazoles. Properties, Biological Activities, and Syntheses

Andreas Schmidt et al.

CURRENT ORGANIC CHEMISTRY (2011)

Article Chemistry, Organic

Synthesis of Pyrazoles via Electrophilic Cyclization

Metin Zora et al.

JOURNAL OF ORGANIC CHEMISTRY (2011)

Article Chemistry, Organic

Synthesis of Pyrazoles via Cul-Mediated Electrophilic Cyclizations of α,β-Alkynic Hydrazones

Metin Zora et al.

JOURNAL OF ORGANIC CHEMISTRY (2011)

Article Chemistry, Applied

Water Mediated Construction of Trisubstituted Pyrazoles/Isoxazoles Library Using Ketene Dithioacetals

Mahesh M. Savant et al.

JOURNAL OF COMBINATORIAL CHEMISTRY (2010)

Article Chemistry, Medicinal

Factor Xa Inhibitors: Next-Generation Antithrombotic Agents

Donald J. P. Pinto et al.

JOURNAL OF MEDICINAL CHEMISTRY (2010)

Review Chemistry, Organic

Recent developments in the chemistry of sydnones

Duncan L. Browne et al.

TETRAHEDRON (2010)

Review Chemistry, Organic

1,3-dipolar cycloadditions of acetylenic sulfones in solution and on solid supports

Detian Gao et al.

JOURNAL OF ORGANIC CHEMISTRY (2008)