Synthetic Access to 1,3-Butadiynes via Electro-redox Cuprous-Catalyzed Dehydrogenative C sp -C sp Homocoupling of Terminal Acetylenes

Article Chemistry, Medicinal

Design and Synthesis of 1,3-Diynes as Potent Antifungal Agents against Aspergillus fumigatus

Lakshmi Goswami et al.

Summary: Researchers synthesized 1,6-diphenoxyhexa-2,4-diyne derivatives and evaluated their antifungal activity. One compound showed promising antifungal activity, suggesting potential for developing new antifungal agents.

CHEMMEDCHEM (2023)

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Article Chemistry, Organic

Electrochemically Generated Copper(I)-Catalyzed Click Chemistry: Triazole Synthesis and Insights into Their Photophysical Properties

Murugan Krishnan et al.

Summary: In this study, we present a novel electro-click (e-CLICK) reaction using electrochemically generated copper(I) catalytic species. The reaction involves the use of copper(II) nitrate and 2,2'-bipyridine as pre-catalyst and ligand, respectively, and proceeds under constant potential electrolysis (-0.25 V). The e-CLICK methodology allows for the synthesis of 1,2,3-triazoles with high yields and excellent regioselectivity, without the need for external reducing agents such as sodium ascorbate.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2023)

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Review Electrochemistry

Electrochemically Enabled Total Syntheses of Natural Products

Chad E. Hatch et al.

Summary: Electrochemical techniques have played a crucial role in the total synthesis of natural products since the pioneering work of Kolbe in the mid 1800s. These techniques have expanded over time, changing the way chemists approach and think about natural products. This review provides a perspective on the use of electrochemical techniques in enabling carbon-carbon bond formations in the assembly of important natural products, discussing mechanistic details and showcasing representative examples from the past few decades. These bond formations offer unique possibilities compared to conventional chemistries, allowing for complementary synthetic strategies.

CHEMELECTROCHEM (2023)

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Article Energy & Fuels

Viologen-based covalent organic polymers: Variation of morphology and evaluation of their ultra-long cycle supercapacitor performance

Bebin Ambrose et al.

Summary: Supercapacitor devices have become increasingly important in energy storage applications due to their excellent power density, quick charging/discharging capabilities, and long cycle ability. This study focuses on the synthesis of two different viologen-based covalent organic polymers (COPs) with hollow sphere and hollow tube morphologies, which show improved stability and enhanced performance compared to traditional polymer electrodes. One of the COPs, COP-2, exhibits remarkable electrochemical performance and exceptional stability with 100% capacitance retention after 50,000 cycles.

JOURNAL OF ENERGY STORAGE (2023)

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Article Chemistry, Inorganic & Nuclear

Flexible three-dimensional diacetylene functionalized covalent organic frameworks for efficient iodine capture

Junyan Zou et al.

Summary: This study successfully synthesized two functionalized three-dimensional covalent organic frameworks (COFs), namely CPOF-2 and CPOF-3, which were functionalized with acetylene (-C(sic)C-) and diacetylene (-C(sic)C-C(sic)C-), respectively. These COFs exhibit high crystallinity, permanent porosity, and chemical stability. Particularly, CPOF-3 demonstrates an extremely high iodine adsorption capacity, up to 5.87 g g(-1), which is much higher than most reported COF-based iodine adsorbents. Therefore, this study provides a new design principle for high-performance iodine adsorption porous materials to address the environmental pollution caused by radioactive iodine in the waste of the nuclear industry.

DALTON TRANSACTIONS (2023)

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Article Electrochemistry

Impact of Ligand in Bimetallic Co, Ni-Metal-Organic Framework towards Oxygen Evolution Reaction

Bebin Ambrose et al.

Summary: In this study, a NiCo-based benzene tricarboxylic (BTC) electrocatalyst was synthesized and its properties were optimized by adding 4,4'-bipyridine as a second ligand, which improved the charge transfer kinetics through non-covalent 7C-7C interaction. The electrocatalyst showed exceptional performance in the oxygen evolution reaction (OER) at different concentrations of KOH. It exhibited low overpotentials and Tafel slope values compared to other catalysts, and demonstrated long-term durability.

ELECTROCHIMICA ACTA (2023)

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Article Biochemistry & Molecular Biology

A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction

Jie Liu et al.

Summary: In this study, an economical method was developed for the synthesis of symmetric diynes using a Cu-catalyzed Glaser reaction with a simple bis-N-heterocyclic carbene ligand. High product yields were obtained for various substrates, including aliphatic and aromatic terminal alkynes. The established protocol is operationally simple and can be carried out in air under base-free conditions.

MOLECULES (2023)

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Article Chemistry, Multidisciplinary

Efficient Ru-Catalyzed Electrochemical Homo- and Heterocoupling Reaction of Terminal Alkynes: Synthesis, In Vitro Anticancer Activity, and Docking Study

Kashyap J. Tamuli et al.

Summary: In this study, ruthenium-catalyzed electrochemical homo- and heterocoupling reactions of terminal alkynes were developed for the synthesis of anticancer drugs. The synthesized compounds were evaluated for their anticancer activity and docking studies were performed to examine their binding affinity with ovarian cancer targets.

ACS OMEGA (2023)

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Article Engineering, Chemical

Practical Coprecipitation Approach for High-Aspect Ratio Cupric Oxide Nanoparticles: A Sustainable Catalytic Platform for Huisgen and Fluorogenic Click Chemistry

Sugirdha Sampath et al.

Summary: In this study, a practical coprecipitation method was developed for the synthesis of cupric oxide nanoparticles. The nanoparticles showed high aspect ratio and were characterized comprehensively. The prepared CuO nanoparticles exhibited excellent catalytic activity in a heterogeneous reaction. The method also enabled the synthesis of fluorogenic clickates with attractive optoelectrochemical properties.

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH (2022)

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Review Energy & Fuels

Direct and Indirect Electro-Oxidative Intramolecular C-H Aminations

Huiqiao Wang et al.

Summary: The lack of metal catalysts is of considerable importance for constructing C-N bonds, as N-heterocycles are ubiquitous in marketed drugs. Electro-oxidative intramolecular C-H amination has emerged as an environmentally friendly method for synthesizing nitrogen-containing heterocycles under metal- and external oxidant-free conditions. This minireview summarizes the main achievements in this direction since 2020, with a focus on substrate scope and mechanistic aspects.

TRANSACTIONS OF TIANJIN UNIVERSITY (2022)

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Review Chemistry, Organic

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

Suman Devi et al.

Summary: Heterocyclic compounds have extensive applications in agrochemicals, pharmaceuticals, and organic materials. The development of electro-organic synthesis has revolutionized the field by replacing traditional methodologies with metal and strong oxidant-free single-step protocols. This review provides an overview of recent advancements and mechanistic descriptions in the synthesis of heterocycles using electrochemical methods, offering insights for future applications.

ORGANIC & BIOMOLECULAR CHEMISTRY (2022)

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Review Chemistry, Multidisciplinary

Reproducibility in Electroorganic Synthesis-Myths and Misunderstandings

Sebastian B. Beil et al.

Summary: The use of electric current as a traceless activator and reagent is experiencing a resurgence in the field of organic chemistry. With researchers from diverse scientific backgrounds entering this field, there is a diversity in reported parameters and methods, potentially impacting the reproducibility of electroorganic syntheses. This Review provides guidelines to streamline experimental parameters and improve reproducibility in the field.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Organic Electrochemistry: Molecular Syntheses with Potential

Cuiju Zhu et al.

Summary: Organic electrosynthesis has emerged as a sustainable platform for molecular assembly, showcasing exceptional selectivities, synergies with photocatalysis or dual electrocatalysis, and novel mechanisms in metallaelectrocatalysis.

ACS CENTRAL SCIENCE (2021)

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Review Chemistry, Multidisciplinary

Reaching the Full Potential of Electroorganic Synthesis by Paired Electrolysis

Wenzhao Zhang et al.

Summary: Electroorganic synthesis is a rapidly developing research area within organic synthesis, focusing on paired electrolysis for simultaneous oxidation and reduction reactions to maximize atom and energy efficiency.

CHEMICAL RECORD (2021)

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Article Chemistry, Multidisciplinary

Construction of Interlayer Conjugated Links in 2D Covalent Organic Frameworks via Topological Polymerization

Yuhao Zhu et al.

Summary: A new interlayer topological polymerization strategy was proposed to transform diacetylene columnar arrays in 2D COFs into conjugated enyne chains upon heating in the solid state, leading to enhanced conductivity and improved photothermal, photoacoustic, and oxygen reduction catalytic performance of the resulting COFs.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Physical

Molecularly engineered oxygen deficient magnetite decorated carbon as electrocatalysts for oxygen reduction reaction

Ramakrishnan Velmurugan Adith et al.

Summary: The in situ synthesis of PFUA was reported by reacting specific compounds, which were then pyrolyzed to obtain magnetically materials with different properties. Among them, PFUA pyrolyzed at 800 degrees C showed the best electrocatalytic activity towards ORR.

MOLECULAR CATALYSIS (2021)

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Article Energy & Fuels

Electrochemical reduction of CO2: Two- or three-electrode configuration

Abebe Reda Woldu et al.

INTERNATIONAL JOURNAL OF ENERGY RESEARCH (2020)

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Review Chemistry, Multidisciplinary

Electrochemical Oxidation of Organic Molecules at Lower Overpotential: Accessing Broader Functional Group Compatibility with Electron-Proton Transfer Mediators

Fei Wang et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

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Review Chemistry, Multidisciplinary

Powering the Future: How Can Electrochemistry Make a Difference in Organic Synthesis?

Tjark H. Meyer et al.

CHEM (2020)

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Article Chemistry, Multidisciplinary

Electro-organic synthesis - a 21st century technique

Dennis Pollok et al.

CHEMICAL SCIENCE (2020)

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Article Chemistry, Multidisciplinary

Ligand and additive free aerobic synthesis of diynes using Pd-CuFe2O4 magnetic nanoparticles as an efficient reusable catalyst

Rituparna Chutia et al.

NEW JOURNAL OF CHEMISTRY (2020)

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Review Chemistry, Organic

Halogen-mediated electrochemical organic synthesis

Hai-Tao Tang et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach

Xiaohan Ye et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Harnessing the TEMPO-Catalyzed Aerobic Oxidation for Machetti-De Sarlo Reaction toward Sustainable Synthesis of Isoxazole Libraries

Murugan Vadivelu et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Multidisciplinary Sciences

A merged copper(I/II) cluster isolated from Glaser coupling

Siqi Zhang et al.

NATURE COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Electropolymerization of thienyl tethered comonomers and application towards the electrocatalytic reduction of nitrobenzene

Abbasriyaludeen Abdul Raheem et al.

RSC ADVANCES (2019)

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Article Chemistry, Multidisciplinary

Metallomicelle catalyzed aerobic tandem desilylation/Glaser reaction in water

Shanyu Tang et al.

GREEN CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Electrochemical synthesis of copper(i) acetylides via simultaneous copper ion and catalytic base electrogeneration for use in click chemistry

Peter W. Seavill et al.

RSC ADVANCES (2019)

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Article Chemistry, Multidisciplinary

Supercritical water assisted preparation of recyclable gold nanoparticles and their catalytic utility in cross-coupling reactions under sustainable conditions

Abbasriyaludeen Abdul Raheem et al.

NANOSCALE ADVANCES (2019)

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Article Chemistry, Physical

Investigations into the mechanism of copper-mediated Glaser-Hay couplings using electrochemical techniques

Peter W. Seavill et al.

FARADAY DISCUSSIONS (2019)

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Article Chemistry, Multidisciplinary

Electrochemical preparation and applications of copper(i) acetylides: a demonstration of how electrochemistry can be used to facilitate sustainability in homogeneous catalysis

Peter W. Seavill et al.

GREEN CHEMISTRY (2018)

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Review Chemistry, Multidisciplinary

Flow Electrolysis Cells for the Synthetic Organic Chemistry Laboratory

Derek Pletcher et al.

CHEMICAL REVIEWS (2018)

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Article Chemistry, Multidisciplinary

Facile route for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazole using copper nanoparticles supported on nanocellulose as recyclable heterogeneous catalyst

Mitali Chetia et al.

JOURNAL OF CHEMICAL SCIENCES (2017)

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Article Chemistry, Organic

Highly Efficient Cycloaddition Reaction of 1,3-Diynes with Sodium Azide: A New Way to 5-Substituted-4-acetylene-1H-1,2,3-triazoles

Jia-Liang Tang et al.

JOURNAL OF HETEROCYCLIC CHEMISTRY (2016)

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Article Biochemistry & Molecular Biology

The Homocoupling Reaction of Aromatic Terminal Alkynes by a Highly Active Palladium(II)/AgNO3 Cocatalyst in Aqueous Media Under Aerobic Conditions

Mengping Guo et al.

MOLECULES (2016)

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Article Chemistry, Physical

Electrical conductivity of solutions of copper(II) nitrate crystalohydrate in dimethyl sulfoxide

Aigul K. Mamyrbekova et al.

RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY A (2016)

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Article Chemistry, Physical

Copper(I) chloride catalysed room temperature C-sp-C-sp homocoupling of terminal alkynes mediated by visible light

Arunachalam Sagadevan et al.

CATALYSIS SCIENCE & TECHNOLOGY (2016)

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Article Chemistry, Multidisciplinary

Soluble Silver Acetylide for the Construction and Structural Conversion of All-Alkynyl-Stabilized High-Nuclearity Homoleptic Silver Clusters

Rui Zhang et al.

CRYSTAL GROWTH & DESIGN (2015)

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Review Chemistry, Multidisciplinary

Redox catalysis in organic electrosynthesis: basic principles and recent developments

Robert Francke et al.

CHEMICAL SOCIETY REVIEWS (2014)

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Article Chemistry, Multidisciplinary

Cu(II)-Cu(I) Synergistic Cooperation to Lead the Alkyne C-H Activation

Ruopeng Bai et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Chemistry, Organic

Convenient Practical Alkynylation of Heteronucleophiles with Copper Acetylides

Cedric Theunissen et al.

SYNTHESIS-STUTTGART (2014)

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Article Chemistry, Organic

1,3-Diyne chemistry: synthesis and derivations

Wei Shi et al.

TETRAHEDRON LETTERS (2014)

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Article Chemistry, Multidisciplinary

Layered graphitic materials from a molecular precursor

Isabelle Levesque et al.

CHEMICAL SCIENCE (2014)

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Article Chemistry, Organic

The Glaser-Hay Reaction: Optimization and Scope Based on 13C NMR Kinetics Experiments

Mie H. Vilhelmsen et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2013)

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Article Chemistry, Multidisciplinary

Mesoporous silica-supported copper-catalysts for homocoupling reaction of terminal alkynes at room-temperature

Hongling Li et al.

NEW JOURNAL OF CHEMISTRY (2013)

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Article Chemistry, Organic

A facile copper(I)-catalyzed homocoupling of terminal alkynes to 1,3-diynes with diaziridinone under mild conditions

Yingguang Zhu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2013)

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Article Multidisciplinary Sciences

Direct Evidence of a Dinuclear Copper Intermediate in Cu(I)-Catalyzed Azide-Alkyne Cycloadditions

B. T. Worrell et al.

SCIENCE (2013)

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Article Electrochemistry

Electrochemical monitoring of the oxidative coupling of alkynes catalyzed by triphenylphosphine gold complexes

Antonio Domenech et al.

ELECTROCHEMISTRY COMMUNICATIONS (2012)

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Article Chemistry, Organic

Discovery of a Robust and Efficient Homogeneous Silver(I) Catalyst for the Cycloaddition of Azides onto Terminal Alkynes

James McNulty et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2012)

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Article Chemistry, Physical

Synthesis of diphenyl-diacetylene-based nematic liquid crystals and their high birefringence properties

Yuki Arakawa et al.

JOURNAL OF MATERIALS CHEMISTRY (2012)

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Article Chemistry, Organic

Site-selective sequential coupling reactions controlled by Electrochemical Reaction Site Switching: a straightforward approach to 1,4-bis(diaryl)buta-1,3-diynes

Koichi Mitsudo et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2012)

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Article Chemistry, Organic

Importance of bases on the copper-catalyzed oxidative homocoupling of terminal alkynes to 1,4-disubstituted 1,3-diynes

Xinjiang Niu et al.

TETRAHEDRON LETTERS (2012)

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Article Chemistry, Multidisciplinary

The First Well-Defined Silver(I)-Complex-Catalyzed Cycloaddition of Azides onto Terminal Alkynes at Room Temperature

James McNulty et al.

CHEMISTRY-A EUROPEAN JOURNAL (2011)

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Article Chemistry, Multidisciplinary

Copper-catalyzed oxidative alkyne homocoupling without palladium, ligands and bases

Xueshun Jia et al.

GREEN CHEMISTRY (2011)

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Article Chemistry, Multidisciplinary

CuCl-catalyzed green oxidative alkyne homocoupling without palladium, ligands and bases

Kun Yin et al.

GREEN CHEMISTRY (2011)

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Article Chemistry, Organic

Hydro-amination/-amidation of 1,3-diynes with indoles/azoles/amides under modified Ullmann conditions: stereo- and regio-selective synthesis of N-alkenynes via N-H bond activation

Sahaj Gupta et al.

TETRAHEDRON LETTERS (2011)

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Article Chemistry, Applied

Copper(I) Acetate: A Structurally Simple but Highly Efficient Dinuclear Catalyst for Copper-Catalyzed Azide-Alkyne Cycloaddition

Changwei Shao et al.

ADVANCED SYNTHESIS & CATALYSIS (2010)

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Review Chemistry, Multidisciplinary

Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper(I) acetylides

Jason E. Hein et al.

CHEMICAL SOCIETY REVIEWS (2010)

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Article Chemistry, Physical

Room-Temperature Ferromagnetism of Flowerlike CuO Nanostructures

Daqiang Gao et al.

JOURNAL OF PHYSICAL CHEMISTRY C (2010)

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Article Chemistry, Organic

Requirement for an oxidant in Pd/Cu co-catalyzed terminal alkyne homocoupling give symmetrical 1,4-disubstituted 1,3-diynes

AS Batsanov et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

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Review Electrochemistry

A century of organic electrochemistry

H Lund

JOURNAL OF THE ELECTROCHEMICAL SOCIETY (2002)

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Synthetic Access to 1,3-Butadiynes via Electro-redox Cuprous-Catalyzed Dehydrogenative C sp -C sp Homocoupling of Terminal Acetylenes

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