☆ 4.5 Review

Recent Advances in Electrochemical Cascade Cyclization Reactions

SYNTHESIS-STUTTGART (2023)

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Article Chemistry, Multidisciplinary

Electrochemical Decarboxylative Cyclization of α-Amino-Oxy Acids to Access Phenanthridine Derivatives

Yanling Zhan et al.

Summary: A method for accessing phenanthridine derivatives via electrochemical decarboxylative cyclization of alpha-amino-oxy acids was developed in this work. The reaction proceeded through iminyl radical formation cascade intramolecular cyclization from readily available materials under environmentally friendly conditions, resulting in a variety of phenanthridine derivatives in moderate to high yields.

CHEMISTRY-AN ASIAN JOURNAL (2022)

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Article Chemistry, Organic

Electro-Oxidative sp(3) C-H Bond Functionalization and Annulation Cascade: Synthesis of Novel Heterocyclic Substituted Indolizines

Bhanwar Kumar Malviya et al.

Summary: This study reports a novel electro-oxidative cascade cyclization reaction, using electricity as the primary energy input, to synthesize a series of indolizine derivatives. This method provides a new strategy for generating heterocyclic diversity of indolizines.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

Electrochemical Sulfonylation-Induced Lactonization of Alkenes: Synthesis of Sulfonyl Phthalides

Jiajun Yang et al.

Summary: An electrochemical cascade sulfonylation and lactonization process using arylsulfonyl hydrazines as the reactants and alkenes as substrates was developed for the first time. This method avoids the use of toxic metal catalysts or stoichiometric oxidants and can be carried out under mild conditions. The desired gamma-sulfonylated phthalides with broad substrate tolerance were successfully obtained.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Paired electrolysis enabled annulation for the quinolyl-modification of bioactive molecules

Shiqi You et al.

Summary: This study reports a paired electrolysis-enabled cascade annulation for the efficient synthesis of highly functionalized quinoline-substituted bioactive molecules. By using this method, two goals, direct synthesis of quinolines and introduction of quinoline moieties to bioactive molecules, can be achieved simultaneously in a single operation. The unique possibilities of electrochemical activation methods are highlighted through the use of electroreduction for the activation of isatin and further anodic oxidation of KI to catalytically result in a cascade annulation. This transformation can tolerate a wide range of functional groups and can be used as a functionalization tactic in pharmaceutical research as well as other areas.

CHEMICAL SCIENCE (2022)

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Article Chemistry, Multidisciplinary

Electrochemical [4+1] Tandem sp3(C-H) Double Amination for the Direct Synthesis of 3-Acyl-Functionalized Imidazo[1,5-a]pyridines

Qiang Wang et al.

Summary: In this study, a one-step electrochemical tandem sp(3)(C-H) double amination was developed for the efficient synthesis of 3-acyl imidazo[1,5-a]pyridines, eliminating the need for the conventional three-step reaction.

ACS OMEGA (2022)

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Article Chemistry, Multidisciplinary

Catalyst-free, direct electrochemical trifluoromethylation/cyclization of N-arylacrylamides using TfNHNHBoc as a CF3 source

Han Wang et al.

Summary: A new electrochemical strategy for trifluoromethylation/cyclization using TfNHNHBoc as a CF3 source has been developed. This approach involves the direct electrolysis of TfNHNHBoc under external oxidant-free and catalyst-free conditions, leading to the formation of various trifluoromethylated oxindoles with good functional group compatibility and broad substrate scope.

CHINESE CHEMICAL LETTERS (2022)

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Article Chemistry, Organic

Electrochemically Enabled Cascade Cyclization Reaction of Aromatic Aldehydes and Pyrazol-5-amines: Synthesis of Bis- pyrazolo[3,4-b:4',3'-e]pyridines

Peng Qian et al.

Summary: A facile method for the synthesis of bis-pyrazolo[3,4-b:4',3'-e]pyridines from easily available aromatic aldehydes and pyrazol-5-amines was developed via electrochemistry, resulting in moderate yields.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Electrochemical Palladium-Catalyzed Oxidative Carbonylation-Cyclization of Enallenols

Jianwei Zhang et al.

Summary: Here we describe an electrochemical oxidative palladium-catalyzed carbonylation-carbocyclization reaction for the synthesis of gamma-lactones and spirolactones, exhibiting excellent chemoselectivity. Interestingly, electrocatalysis was found to enhance the reaction rate of the tandem process, leading to a more efficient reaction compared to chemical redox conditions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Organic

Electrochemical Synthesis of Polysubstituted Sulfonated Pyrazoles via Cascade Intermolecular Condensation, Radical-Radical Cross Coupling and Annulation

Jiajun Feng et al.

Summary: In this study, an metal-free, exogenous-oxidant-free, and mild conditions electrochemical synthesis of polysubstituted sulfonated pyrazoles was developed. NH2-functionalized enaminones or N,N-disubstituted enaminones reacted with aryl/alkyl sulfonyl hydrazides to produce tetra- or trisubstituted sulfonated pyrazoles in moderate to good yields, respectively. The gram-scale electro-chemical transformation demonstrated the efficiency and practicability of this method. The formation mechanism involves intermolecular condensation, radical-radical cross coupling sulfonylation, and pyrazole annulation.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Article Chemistry, Organic

An electrochemical tandem Michael addition, azidation and intramolecular cyclization strategy for the synthesis of imidazole derivatives

Kai Zhou et al.

Summary: An electrochemical-oxidation-induced intramolecular annulation method was developed for the synthesis of imidazole. This method allowed amines, alkynes, and azides to smoothly participate in the reaction, resulting in various substituted imidazoles through a tandem Michael addition/azide/cycloamine reaction. The reaction was easily conducted without the need for transition metal catalysts and peroxide reagents, demonstrating its adherence to the principles of green chemistry.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Electrochemical triamination of alkynes: controllable synthesis of functionalized indolines and indoles

Xiangtai Meng et al.

Summary: This article reports an unprecedented electrocatalyic triamination of alkynes via N-H cleavage. Using TEMPO as the catalyst, this reaction allows controllable access to a variety of 2,3-diimino indolines and 2,3-diamino indoles. The reaction avoids the use of terminal oxidants, transition metals, and explosive reagents.

GREEN CHEMISTRY (2022)

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Article Chemistry, Organic

Electrochemical oxidative selenocyclization of olefinic amides towards the synthesis of iminoisobenzofurans

Hao Li et al.

Summary: Organoselenium compounds are important in medicinal chemistry, materials chemistry, and biochemistry. The selenation of pharmaceutical molecules is a promising method for discovering new drugs. This study introduces an electrochemical oxidative radical cascade cyclization of olefinic amides and diselenides without the need for transition-metal catalysts and external oxidants, resulting in high yields of desired products.

ORGANIC CHEMISTRY FRONTIERS (2022)

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Article Chemistry, Applied

Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N-arylacrylamides with Diorganyl Diselenides

Xin-Yu Wang et al.

Summary: The article describes a novel method for tandem cyclization of acrylamide with diselenides facilitated by electrochemical oxidation, successfully synthesizing pharmacologically active seleno oxindoles, which exhibited excellent in vitro antitumor activity.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Multidisciplinary

Direct Electrochemical Synthesis of Sulfur-Containing Triazolium Inner Salts

Yueheng Li et al.

Summary: In this study, an electrochemical thiocyanation/cyclization of aldehyde hydrazones was developed under external oxidant-free and catalyst-free conditions, utilizing commercially available and inexpensive sodium thiocyanate as a dual role reagent and electrolyte. This strategy provides expedient access to functionalized sulfur-containing triazolium inner salts with ample scope and diverse functional group tolerance. Based on mechanistic studies, a reaction mechanism was proposed.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Highly Diastereoselective Synthesis of Dihydro-benzoimidazo-[1,3]-thiazines via Electro-oxidative Selenocyclization of Thioallyl Benzoimidazoles

Atreyee Halder et al.

Summary: The methodology involves a green and efficient electro-oxidative tandem selenocyclization of thioallyl benzoimidazoles to produce selenylated dihydro-benzoimidazo-thiazine derivatives. Both C-Se and C-N bond formation are achieved with up to 96% isolated yields. The method exhibits good functional group tolerability and complete control over regioselective formation of the six-membered heterocycle.

CHEMISTRY-AN ASIAN JOURNAL (2021)

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Article Chemistry, Organic

Oxidant- and Catalyst-Free Synthesis of Sulfonated Benzothiophenes via Electrooxidative Tandem Cyclization

Dong Zhang et al.

Summary: A green and practical electrochemical method has been developed for the synthesis of C-3-sulfonated benzothiophenes, achieving moderate to good yields of compounds with important functional groups. Mechanistic studies suggest a tandem radical addition-cyclization pathway, and the protocol is easy to scale up with good reaction efficiency.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Applied

Transition Metal-Free Synthesis of Sulfonyl- and Bromo-Substituted Indolo[2,1-α]isoquinoline Derivatives through Electrochemical Radical Cascade Cyclization

Zheng-Jia Shen et al.

Summary: A tunable electrosynthesis of sulfonyl- and bromo-substituted indolo[2,1-alpha]isoquinoline derivatives has been developed, offering valuable compounds in moderate to good yields. This reaction proceeds via a radical cascade cyclization pathway and features broad substrate scope and good functional group tolerance under transition metal-free and oxidant-free conditions.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Organic

Synthesis of Polysubstituted Furans through Electrochemical Selenocyclization of Homopropargylic Alcohols

Debabrata Maiti et al.

Summary: The mild and efficient electrochemically driven synthetic route allows for the access of polysubstituted selenofuran derivatives through diselenide-promoted cyclization of homopropargyl alcohols, with up to 84% isolated yield. This methodology demonstrates good functional group compatibility and further conversion to valuable furan derivatives.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Manganese-catalyzed Electro-oxidative Azidation-annulation Cascade to Access Oxindoles and Quinolinones

Debabrata Maiti et al.

Summary: An environmentally friendly and efficient electro-oxidative tandem azidation-radical cyclization strategy was reported, utilizing manganese-catalyzed electrochemical reaction in an undivided cell at room temperature and the use of NaN3 as the cheapest azide source. This protocol successfully synthesized a series of oxindole and quinolinone derivatives, with the azide functionality efficiently converted to various valuable derivatives.

CHEMISTRY-AN ASIAN JOURNAL (2021)

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Article Chemistry, Multidisciplinary

Organocatalytic Electrosynthesis of Cinnolines through Cascade Radical Cyclization and Migration

Chen Cai et al.

Summary: A green and mild reaction condition has been developed for the synthesis of cinnoline derivatives with good to excellent yield and broad functional group tolerance. The method also shows excellent regioselectivity and proposes a possible electrochemically cascade radical cyclization and migration process.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2021)

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Article Chemistry, Organic

Electrochemical Tandem Cyclization of Unsaturated Oximes with Diselenides: A General Approach to Seleno Isoxazolines Derivatives with Quaternary Carbon Center

Wenchao Gao et al.

Summary: An electrochemical oxidative tandem cyclization of unsaturated oximes with diselenides has been developed, providing a general access to seleno isoxazolines containing a quaternary carbon center (35 examples). This novel protocol features mild reaction conditions (metal- and oxidant-free), good functional group tolerance, and promising scalability, with plausible reaction pathways proposed.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Electrochemical oxidative radical cascade cyclization of olefinic amides and thiophenols towards the synthesis of sulfurated benzoxazines, oxazolines and iminoisobenzofurans

Fangling Lu et al.

Summary: A new electrochemical oxidative strategy was introduced to construct heterocycles containing N and O without the need for a transition-metal catalyst and an external oxidant. Various olefinic amides and thiophenols/diselenides were reacted in a simple undivided cell to produce thiolation and selenylation heterocycles in up to 83% yields, providing a facile method for constructing C-S/C-Se and C-O bonds in one step.

GREEN CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Electro-oxidative cyclization: access to quinazolinones via K2S2O8 without transition metal catalyst and base

Yongzhi Hu et al.

Summary: The oxidative tandem cyclization of primary alcohols with 2-aminobenzamides to synthesize quinazolinones using K2S2O8 as a radical surrogate under undivided electrolytic conditions is a green, mild, and practical method with high efficiency and excellent functional group tolerance. The use of continuous-flow electrochemical setups allows for easy scalability of the reaction.

RSC ADVANCES (2021)

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Article Chemistry, Multidisciplinary

Electrochemical trifluoromethylation/cyclization for the synthesis of isoquinoline-1,3-diones and oxindoles

Yuanqiang Guo et al.

Summary: The protocol described in this study utilizes electrochemical cathode reduction to generate trifluoromethyl radicals using an inexpensive and readily available trifluoromethylation reagent (IMDN-SO2CF3). The reaction can be efficiently conducted without the need for additional redox reagents, allowing for electrochemical trifluoromethylation/cyclization for the synthesis of isoquinoline-1,3-diones and oxindoles. This strategy demonstrates good functional group tolerance and a broad substrate scope.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

Electrochemical NaI/NaCl-mediated one-pot synthesis of 2-aminobenzoxazoles in aqueous media via tandem addition-cyclization

Thao Nguyen Thanh Huynh et al.

Summary: An electrochemical synthesis of 2-aminobenzoxazoles from 2-aminophenols and isothiocyanates using NaI and NaCl as catalysts in an open-flask undivided cell provides various products in moderate to high yields. This method is also applicable to the synthesis of 2-aminobenzothiazoles and has the benefits of being metal-free, scalable, and environmentally friendly.

GREEN CHEMISTRY (2021)

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Article Chemistry, Organic

Electrochemical oxidative synthesis of 1,3,4-thiadiazoles from isothiocyanates and hydrazones

Zhongxiao Ma et al.

Summary: The method demonstrated here involves a DDQ-catalysed electrochemical synthesis of 2-amino-1,3,4-thiadiazoles from isothiocyanates and hydrazones. The protocol is mild, practical, metal-free, and exogenous oxidant-free, with extensive mechanistic investigations revealing that the reaction proceeds via a tandem addition/chemoselective C-S coupling sequence. Additionally, it is the hydrogenated DDQ that is oxidized at the anode, not the intermediate thiosemicarbazides.

ORGANIC CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Organic

Electrochemical synthesis of sulfonated benzothiophenes using 2-alkynylthioanisoles and sodium sulfinates

Ming-Ming Zhang et al.

Summary: A method for electrochemical sulfonylation/cyclization of 2-alkynylthioanisoles with sodium sulfinates under catalyst-, external oxidant- and metal-free conditions has been developed, offering sustainable and efficient access to 3-sulfonated benzothiophenes with good substrate scope and functional group tolerance. This cascade radical process is triggered through a sulfonyl radical addition to alkynes using sodium sulfinates under electrochemical conditions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Catalyst-free synthesis of phenanthridines via electrochemical coupling of 2-isocyanobiphenyls and amines

Bhanwar Kumar Malviya et al.

Summary: This study reports a catalyst-free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction. Detailed mechanistic studies revealed that the coupling reaction proceeds by the cathodic reduction of in situ formed diazonium ions, which then coupled with isocyanides to furnish the desired products in good yields.

NEW JOURNAL OF CHEMISTRY (2021)

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Article Chemistry, Applied

Electrochemical Chalcogenation of β,γ-Unsaturated Amides and Oximes to Corresponding Oxazolines and Isoxazolines

Samrat Mallick et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Electrochemical Access to Aza-Polycyclic Aromatic Hydrocarbons: Rhoda-Electrocatalyzed Domino Alkyne Annulations

Wei-Jun Kong et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

CF3SO2Na as a Bifunctional Reagent: Electrochemical Trifluoromethylation of Alkenes Accompanied by SO2 Insertion to Access Trifluoromethylated Cyclic N-Sulfonylimines

Zheng Li et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Organic

Electrochemical HI-mediated Intermolecular C-N Bond Formation to Synthesize Imidazoles from Aryl Ketones and Benzylamines

Zan Yang et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Physical

Mn-Catalyzed Electrochemical Radical Cascade Cyclization toward the Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolin-6(5H)-one Derivatives

Yong Yuan et al.

ACS CATALYSIS (2020)

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Article Chemistry, Organic

Electrochemical Annulation-lodosulfonylation of 1,5-Enyne-containing para-Quinone Methides (p-QMs) to Access (E)-Spiroindenes

Hang-Dong Zuo et al.

ORGANIC LETTERS (2020)

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Article Electrochemistry

Electro-Generated Acids Catalyzed Epoxyolefin Cyclizations via Cationic Chain Reactions

Kouichi Matsumoto et al.

ELECTROCHEMISTRY (2020)

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Article Chemistry, Organic

Electrochemical Tandem Fluoroalkylation-Cyclization of Vinyl Azides: Access to Trifluoroethylated and Difluoroethylated N-Heterocycles

Long Lin et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

The synthesis of sulfonated 4H-3,1-benzoxazines via an electro-chemical radical cascade cyclization

Tian-Jun He et al.

CHEMICAL COMMUNICATIONS (2020)

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Review Biochemistry & Molecular Biology

Natural product syntheses via carbonylative cyclizations

Kaiqing Ma et al.

NATURAL PRODUCT REPORTS (2019)

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Article Chemistry, Multidisciplinary

Formal Aza-Wacker Cyclization by Tandem Electrochemical Oxidation and Copper Catalysis

Xiangli Yi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade

Hong Yan et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Organic

Mn-Mediated Electrochemical Trifluoromethylation/C(sp2)-H Functionalization Cascade for the Synthesis of Azaheterocycles

Zhenxing Zhang et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Multidisciplinary

De Novo Synthesis of Highly Functionalized Benzimidazolones and Benzoxazolones through an Electrochemical Dehydrogenative Cyclization Cascade

Fan Xu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Electrocatalytic Tandem Synthesis of 1,3-Disubstituted Imidazo[1,5-a]quinolines via Sequential Dual Oxidative C(sp3)-H Amination in Aqueous Medium

Peng Qian et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Electrochemistry

Mn-Catalyzed Electrochemical Synthesis of Quinazolinones from Primary Alcohols/Benzyl Ethers and o-Aminobenzamides

Dian-Zhao Lin et al.

CHEMELECTROCHEM (2019)

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Review Chemistry, Applied

Stereoselective Haliranium, Thiiranium and Seleniranium Ion-Triggered Friedel-Crafts-Type Alkylations for Polyene Cyclizations

Biswajit Maji

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Multidisciplinary

Electrochemical oxidative cyclization of olefinic carbonyls with diselenides

Zhipeng Guan et al.

GREEN CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Electrochemically initiated intermolecular C-N formation/cyclization of ketones with 2-aminopyridines: an efficient method for the synthesis of imidazo[1,2-a]pyridines

Mei-Lin Feng et al.

GREEN CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Electrochemical Synthesis of Imidazo-Fused N-Heteroaromatic Compounds through a C-N Bond-Forming Radical Cascade

Zhong-Wei Hou et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Article Chemistry, Applied

One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies

Liu Cao et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

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Article Chemistry, Organic

Electrochemical synthesis of 7-membered carbocycles through cascade 5-exo-trig/7-endo-trig radical cyclization

Hao Long et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

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Review Chemistry, Multidisciplinary

Oxidative Cyclization in Natural Product Biosynthesis

Man-Cheng Tang et al.

CHEMICAL REVIEWS (2017)

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Article Chemistry, Organic

Electrooxidative Tandem Cyclization of Activated Alkynes with Sulfinic Acids To Access Sulfonated Indenones

Jiangwei Wen et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Physical

Electrochemical Synthesis of Polycyclic N-Heteroaromatics through Cascade Radical Cyclization of Diynes

Zhong-Wei Hou et al.

ACS CATALYSIS (2017)

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Article Chemistry, Multidisciplinary

Access to cyclic gem-difluoroacyl scaffolds via electrochemical and visible light photocatalytic radical tandem cyclization of heteroaryl chlorodifluoromethyl ketones

Cherif Adouama et al.

CHEMICAL COMMUNICATIONS (2017)

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Article Chemistry, Multidisciplinary

Electrochemically catalyzed amino-oxygenation of styrenes: n-Bu4NI induced C-N followed by a C-O bond formation cascade for the synthesis of indolines

Sen Liang et al.

GREEN CHEMISTRY (2016)

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Article Chemistry, Organic

Aryl radical cyclization with alkyne followed by tandem carboxylation in methyl 4-tert-butylbenzoate-mediated electrochemical reduction of 2-(2-propynyloxy)bromobenzenes in the presence of carbon dioxide

Asahi Katayama et al.

TETRAHEDRON (2016)

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Article Chemistry, Organic

Chemical and electrocatalytic cascade cyclization of salicylaldehyde with three molecules of malononitrile: 'one-pot' simple and efficient way to the chromeno[2,3-b]pyridine scaffold

Michail N. Elinson et al.

TETRAHEDRON (2014)

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Article Chemistry, Inorganic & Nuclear

Electroactive oxazoline ligands

Francois Riobe et al.

COORDINATION CHEMISTRY REVIEWS (2010)

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Review Biochemistry & Molecular Biology

2(3H)-benzoxazolone and bioisosters as Privileged Scaffold in the design of pharmacological probes

J Poupaert et al.

CURRENT MEDICINAL CHEMISTRY (2005)

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