Article
Chemistry, Applied
Jin-Lin Wan, Jing-Mei Huang
Summary: An electrochemical oxidative approach for the synthesis of spirooxazolidinones from phenol derivatives via intramolecular dearomative amination reactions is developed. This reaction does not require the use of metal catalysts or external chemical oxidants, and exhibits a broad substrate scope and compatibility with diverse functional groups. The synthetic utility of this strategy is demonstrated through gram-scale synthesis and late-stage functionalization. Additionally, the reaction conditions can be adjusted to produce alcohols (1˚, 2˚, and 3˚) from phenol derivatives, offering a useful strategy for deprotecting the para-methoxyphenyl (PMP) group and recovering the alcohol functionality.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Yong Deng, Shiqi You, Mengyao Ruan, Ying Wang, Zuxing Chen, Guichun Yang, Meng Gao
Summary: This study reports the direct regiodivergent N1/C2 phosphorylation of free indole derivatives under electrochemical conditions without exogenous oxidants and metal catalysts. Different active indole species generated by electrolyte-mediated anodic oxidation led to a diverse collection of phosphorylation products with moderate to high yields. Additionally, N-P coupling was found to be compatible with various alkylamines.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Electrochemistry
Maryam Mehrdadian, Sadegh Khazalpour, Ameneh Amani
Summary: This study investigates the electrochemical oxidation of 3 and 4 substituted catechols, and finds that the resulting p-quinones can react with nucleophiles to form p-quinone imine derivatives.
ELECTROCHIMICA ACTA
(2022)
Article
Chemistry, Organic
Zhong-Wei Hou, Ming-Ming Zhang, Wen-Chao Yang, Lei Wang
Summary: This article describes a novel electrochemical method for the site-selective benzylic C(sp(3))-H oxidation of phenol derivatives, accompanied by the evolution of hydrogen. The protocol can be carried out in an undivided cell at room temperature without the need for catalysts or oxidizing reagents. The corresponding aryl aldehydes and ketones are obtained in satisfactory yields, making gram-scale synthesis easily achievable.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shengsheng Lin, Xiaomei Cheng, Balati Hasimujiang, Zhongnan Xu, Fengtan Li, Zhixiong Ruan
Summary: A metal- and oxidant-free, environmentally friendly protocol for the regioselective selenylation of 2H-indazole derivatives by an electrochemical strategy was developed in this study. Selenylated 2H-indazoles with a wide range of functional groups were synthesized in moderate to good yields under mild and environment-friendly reaction conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kazuki Ohira, Keiichi Imato, Yousuke Ooyama
Summary: Phenazine-2,3-diol derivatives KO-0-3 with varying formyl groups have been developed as photosensitizers capable of generating singlet oxygen. Compared to phenazine-2,3-MOM derivatives 5-8, KO-0-3 show red-shifted photoabsorption bands, lower fluorescence quantum yields, and enhanced ability to generate singlet oxygen under visible light irradiation with increasing formyl groups. The presence of formyl groups facilitates intersystem crossing from the lowest singlet excited states to triplet excited states, providing valuable insights for the molecular design of efficient phenazine-2,3-diol-based photosensitizers for photodynamic therapy.
MATERIALS CHEMISTRY FRONTIERS
(2021)
Article
Electrochemistry
Vladimir Ivanovski, Natalia Festinger, Rafal Karpowicz, Pawel Tokarz, Kaja Spilarewicz, Dariusz Guziejewski, Sylwia Smarzewska
Summary: Differential pulse and cyclic voltammetry were used to investigate the electrocatalytic effects of graphene derivatives on the oxidation mechanism of acemetacin. The morphology and composition of the surface coatings strongly influenced the electroanalysis of ACM. Density functional theory calculations were performed to analyze the electron density and orbital distribution of ACM to determine the most probable oxidation site. Different oxidation mechanisms were preferred at each modifier layer. Calibration curves were developed for both working electrodes to determine the relationship between ACM oxidation mechanism and analytical usability.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2023)
Article
Electrochemistry
Keerakit Kaewket, Chanpen Karuwan, Somchai Sonsupap, Santi Maensiri, Kamonwad Ngamchuea
Summary: In this study, carbon nanofibers (CNF) were synthesized by electrospinning and their anti-fouling properties were demonstrated. The synthesized CNF was characterized using various techniques, and different electrode preparation methods were tested. The electrochemical behaviors of CNF towards various systems were explored, highlighting the material's potential applications.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Ivan V. Smolyaninov, Georgy K. Fukin, Nadezhda T. Berberova, Andrey I. Poddel'sky
Summary: A new series of triphenylantimony(V) complexes with different substituents were synthesized and characterized, showing variations in their crystal structures, electrochemical oxidation behavior, and radical scavenging activities.
Review
Biochemistry & Molecular Biology
Ashwin K. V. Mruthunjaya, Angel A. J. Torriero
Summary: The electrochemical oxidation of amines is an alternative method for chemical transformation, which is crucial for synthesizing and modifying chemically useful molecules such as pharmaceuticals and agrochemicals. This review discusses the mechanism of oxidation for different types of amines, comparing and simplifying the various pathways to understand the overall process. Examples of applications of these oxidation reactions are also provided.
Article
Chemistry, Organic
Wei Zhou, Peng Chen, Zi-Qiong Li, Li-Tong Xiao, Jiang Bai, Xian-Rong Song, Mu-Jia Luo, Qiang Xiao
Summary: This study presents a general electrochemical method for the synthesis of diverse imide derivatives from easily available raw materials, including arylcyclopropanes, acetonitrile, carboxylic acids, and alcohols. The method involves a metal-catalyst- and oxidant-free single-electron oxidation strategy, providing a sustainable and green alternative for the formation of highly reactive cyclopropane-derived radical cations with broad functional group tolerance.
Article
Chemistry, Organic
Wei Zhou, Peng Chen, Zi-Qiong Li, Li-Tong Xiao, Jiang Bai, Xian-Rong Song, Mu-Jia Luo, Qiang Xiao
Summary: This study describes a new electrochemical reaction method for the quick construction of structurally diverse imide derivatives from easily available raw materials. By using arylcyclopropanes, acetonitrile, carboxylic acids, and alcohols in a simple cell, this method offers a green alternative for the formation of highly reactive cyclopropane-derived radical cations, without the need for metal catalysts and oxidants. It also demonstrates broad functional group tolerance.
Article
Biochemistry & Molecular Biology
Marcel Hrubsa, Raul Alva, Mst Shamima Parvin, Katerina Macakova, Jana Karlickova, Jaka Fadraersada, Lukas Konecny, Monika Moravcova, Alejandro Carazo, Premysl Mladenka
Summary: Flavonoids have positive cardiovascular effects, and one of its metabolites, 4-methylcatechol, is a potent antiplatelet compound. In this study, the activity of 22 compounds, including 4-methylcatechol and its derivatives, were compared. Results showed that 17 compounds were highly active in inhibiting platelet aggregation, with 7 of them having an IC50 below 3 mu M. These compounds showed no toxicity to erythrocytes or significant effects on blood coagulation.
Article
Engineering, Electrical & Electronic
Cheng Wang, Rui Wu, Hao Ling, Zhiling Zhao, Wenjia Han, Xiaowen Shi, Gregory F. Payne, Xiaohui Wang
Summary: This study reports a composite paper electrode fabricated through designed papermaking that offers sensitive and selective chemical detection. The composite paper can be electrochemically reduced under relatively mild conditions, enhancing its electrocatalytic properties. Compared to traditional surface modification methods, this composite paper electrode exhibits comparable or even better sensing performance.
NPJ FLEXIBLE ELECTRONICS
(2022)
Article
Chemistry, Physical
Vincent Ball, Maria Laura Alfieri, Kevin Ziegler, Youri Arntz, Marco d'Ischia
Summary: The deposition efficiency and electrochemical properties of coatings obtained from different benzenediols were compared. Resorcinol showed higher deposition efficiency compared to catechol, while hydroquinone did not form detectable coating. Catechol and hydroquinone exhibited reversible electrochemical properties, while resorcinol displayed an irreversible process. The results provide insights for future studies on coating design and tailoring.
SURFACES AND INTERFACES
(2022)
Article
Chemistry, Analytical
Razzagh Rahimpoor, Abdulrahman Bahrami, Davood Nematollahi, Farshid Ghorbani Shahna, Maryam Farhadian
Summary: In this study, a magnetic-dispersive solid-phase extraction (DSPE) method was developed for the extraction and desorption of muconic acid from real urine samples. Fe3O4-SiO2-NH2@ UiO-66 was used as a Metal-Organic Framework (MOF) in the DSPE for extraction followed by HPLC analysis. The method showed good detection limit, wide linear dynamic range, and high correlation coefficient, indicating its efficiency for the extraction and analysis of muconic acid from urine samples.
INTERNATIONAL JOURNAL OF ENVIRONMENTAL ANALYTICAL CHEMISTRY
(2022)
Article
Electrochemistry
Niloofar Mohamadighader, Davood Nematollahi, Mahnaz Saraei
Summary: The electrochemical oxidation of propofol in a water/acetonitrile mixture was studied, revealing a chemically irreversible oxidation process to form propofol dimer. The electrochemical synthesis of PDQ was successfully achieved with the catalytic effect of sulfite ions. This method provides a greener alternative for dimerization of propofol under mild conditions.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2021)
Article
Chemistry, Analytical
Mahmood Masoudi Khoram, Niloofar Mohamadighader, Davood Nematollahi, Sadegh Khazalpour, Hossein Masoumi, Hojjat Alizadeh
Summary: A green electrochemical method was developed for the synthesis of new spiro and dispiro pyrimidine derivatives. The reactivity of the nucleophile (barbituric acids) was found to be crucial in determining the type of product. The synthesized compounds showed good antibacterial performance against gram-positive bacteria.
JOURNAL OF ELECTROANALYTICAL CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Zahra Souri, Mahmood Masoudi Khoram, Davood Nematollahi, Mohammad Mazloum-Ardakani, Hojjat Alizadeh
Summary: Electrochemical oxidation of imipramine in aqueous solutions was studied, showing a complex behavior at different pH values. The oxidation of imipramine at a pH of about 5 led to the formation of a unique dimer, which was fully characterized. A possible reaction mechanism for the oxidation process was proposed. The synthesized dimer exhibited fluorescence activity and good antibacterial performance.
SCIENTIFIC REPORTS
(2022)
Article
Electrochemistry
Faezeh Zivari-Moshfegh, Davood Nematollahi
Summary: A new derivative of desloratadine (DQ-TBC complex) was synthesized for the first time using a green electrochemical method. The electrooxidation of 4-tert-butylcatechol (TBC) in the presence of desloratadine (DES) was investigated to optimize the synthesis conditions of DQ-TBC complex. The results suggest that the electrooxidation of TBC in the presence of DES leads to DQ through an ECE mechanism. The synthesized compound showed promising antibacterial activity against Bacillus cereus and Staphylococcus aureus.
ELECTROCHIMICA ACTA
(2022)
Article
Electrochemistry
Heydar Hameed Salman Arkwazee, Niloofar Mohamadighader, Davood Nematollahi, Arash Rabiee, Hojjat Alizadeh
Summary: This article describes a method for synthesizing new sulfonamide derivatives using electrochemical methods without toxic reagents, and finds that these products have good antibacterial performance against bacteria.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2022)
Article
Electrochemistry
Niloofar Mohamadighader, Davood Nematollahi, Mahnaz Saraei
Summary: Electrochemical oxidation of phenothiazine in an acetonitrile/water mixture was investigated, revealing that the oxidation pathway varies with respect to pH. The results led to the synthesis of two new types of PTZ dimer and provided insights into the oxidation mechanism of PTZ.
ELECTROCHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Razzagh Rahimpoor, Ali Firoozichahak, Saber Alizadeh, Houman Serkan, Davood Nematollahi
Summary: This paper synthesized an aluminum-based metal-organic framework and utilized it in high-performance liquid chromatography for the reliable determination of cyclophosphamide in urine samples. By optimizing various parameters, satisfactory measurement results and recovery rates were obtained.
Article
Electrochemistry
Mohammad Reza Talebi, Davood Nematollahi, Ahmad Reza Massah
Summary: The electrochemical oxidation of N-(4-aminophenyl) and N-(4-hydroxyphenyl)benzenesulfonamide derivatives was investigated at different pH values and concentrations. The oxidation potential and mechanism of these compounds were found to be pH dependent. The oxidation products were found to undergo hydroxylation and/or dimerization reactions. The adsorption behavior and oxidation products under conditions similar to the human body were also studied.
ELECTROCHIMICA ACTA
(2023)
Article
Electrochemistry
Faezeh Zivari-Moshfegh, Fereshteh Javanmardi, Davood Nematollahi
Summary: The electrochemical behavior of rifampicin, an anti-tuberculosis drug, was studied in a water/ethanol mixture. The drug was found to undergo two-step oxidation, with the first step being a reversible oxidation of the hydroquinone moiety and the second step being an irreversible oxidation of the phenolic ring. The adsorption activity and diffusion coefficient of rifampicin were also determined, indicating that the first oxidation step is diffusion-controlled and the second step is a diffusion/adsorption control process. The oxidation of rifampicin was found to be complex and highly pH-dependent, with different rates of reaction observed for different drugs used in combination therapy.
ELECTROCHIMICA ACTA
(2023)
Article
Electrochemistry
Faezeh Zivari-Moshfegh, Davood Nematollahi
Summary: This study investigates the toxic metabolites formed from the oxidation of rifampicin and acetaminophen in the body. It provides strong evidence of a catalytic reaction between vitamin C and the oxidized form of rifampicin. Additionally, contrary to previous reports, this study discovers another catalytic reaction between oxidized acetaminophen and rifampicin.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2023)
Article
Electrochemistry
Zahra Godini, Davood Nematollahi, Faezeh Zivari-Moshfegh
Summary: In this study, the electrochemical complexation of five azole antifungal drugs with silver, copper and zinc cations was conducted in an undivided electrolytic cell. Twenty complexes were synthesized using a simple method in water/ethanol mixtures with high yield and purity. The applied current and acid concentration were found to have no significant effects on the yield and purity of the complexes, but they did affect the cell voltage and energy consumption.
JOURNAL OF THE ELECTROCHEMICAL SOCIETY
(2023)
Article
Multidisciplinary Sciences
Pouria Patoghi, Ali Sadatnabi, Davood Nematollahi
Summary: In this study, a new convergent paired electro-organic synthesis method for sulfonamide derivatives was introduced, which follows the principles of green chemistry and does not require catalysts, oxidants, halogens, or amines. Instead of using toxic amine compounds, an innovative mechanism based on the reduction of nitro compounds and in-situ production of amine compounds was used. The mechanism involves cathodic reduction of nitro compounds to hydroxylamine compounds and anodic oxidation of hydroxylamine compounds to nitroso compounds.
SCIENTIFIC REPORTS
(2023)
Review
Chemistry, Multidisciplinary
Mahdi Jamshidi, Ameneh Amani, Sadegh Khazalpour, Sara Torabi, Davood Nematollahi
Summary: Organic electrochemistry is a modern and efficient field that utilizes eco-friendly and sustainable electrochemical methods for functionalizing organic compounds. This review focuses on the synthesis of organosulfone and sulfonamide derivatives using electrochemical reduction and oxidation techniques, highlighting the mechanisms, parameters, cells, and yields involved in the process.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zahra Tavakkoli, Hamed Goljani, Hassan Sepehrmansourie, Davood Nematollahi, Mohammad Ali Zolfigol
Summary: This study investigated the electrochemical reduction of different aryldiazonium salts in aqueous solution, showing that the process occurs in two single-electron steps. The presence of different substituents on the phenyl ring affects the adsorption characteristics and ease of reduction of the corresponding diazonium salts, with electron withdrawing substituents making the reduction process easier.
