Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: In this study, a gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones was developed using an Al-Li-BINOL (ALB) complex catalyst. The reaction showed high diastereoselectivity with ratios up to 20:1 and enantioselectivity of 84-98% for various substrate combinations. This method is complementary to previous reports and improves selectivity for several chromones. Computational studies support the role of ALB as a bifunctional catalyst in this reaction and provide insights into the origin of the observed stereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Sadhanendu Samanta, Jin Cui, Hidetoshi Noda, Takumi Watanabe, Masakatsu Shibasaki
Summary: A gram-scale syn-selective asymmetric vinylogous addition of butenolides to chromones, catalyzed by an Al-Li-BINOL (ALB) complex, was developed in this study. The diastereoselectivity reached 20:1 with 84-98% ee for various combinations of substrates. This protocol complements previous methods and improves selectivity for multiple chromones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Yuji Nakano, Jeremy T. Maddigan-Wyatt, David W. Lupton
Summary: Conjugate acceptors are commonly used electrophilic functional groups in organic synthesis. Our research focuses on their ability to undergo polarity inversion through the conjugate addition of Lewis base catalysts. We have achieved cycloisomerizations and annulation reactions using simple conjugate acceptors and those embedded within more complicated substrates. However, significant challenges remain to be addressed before a universal approach to polarity inversion of all conjugate acceptors can be achieved.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Article
Chemistry, Analytical
Yujing Zuo, Zhiming Gou, Minggang Tian, Jingting Zhan, Weiying Lin
Summary: Rapid response is an important goal in fluorescence analysis technology, but it is often uncontrollable due to the limitations of the response mechanism and detection targets. In this study, a novel catalyst PNL-Br was synthesized and successfully incorporated into fluorescence analysis, showing a higher catalytic potential in thiol-Michael addition reactions. Notably, PNL-Br was an efficient catalyst for dithiothreitol (DTT) detection by fluorescence analysis, which was the first example of a catalysis system for fluorescent probe detection reactions.
SENSORS AND ACTUATORS B-CHEMICAL
(2023)
Article
Chemistry, Organic
Sanjay Singh, Ravi Saini, Ravi P. Singh
Summary: An unprecedented organocatalyzed asymmetric vinylogous Michael reaction with excellent enantiomeric ratio and yield has been reported. The remarkable selectivity is attributed to the hydrogen bonding ability of the catalyst. The reaction is versatile and practical for the synthesis of various gamma-functionalized coumarin derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Haruna Araki, Shohei Furuya, Kazuya Kanemoto, Shin-ichi Fukuzawa
Summary: The conjugated addition reaction of 1-pyrroline-5-carbonitrile to alpha-enones was effectively catalyzed by AgF/ThioClickFerrophos (TCF) in diethyl ether in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and nearly single diastereomers of adducts with good enantiomeric excesses (up to 97% ee) were obtained in high yields. The reduction of the nitrile group with H2/Raney Ni in ethanol successfully transformed the conjugate adduct to the corresponding spirocyclic piperidine (60% yield) as a single stereoisomer.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Michal Kopyt, Michal Tryniszewski, Michal Barbasiewicz, Piotr Kwiatkowski
Summary: Enantioselective Michael addition under high-pressure conditions is an efficient method to synthesize chiral cyclohexanes.
Article
Chemistry, Applied
Hamidulla B. Tukhtaev, Stanislav I. Bezzubov, Elena A. Tarasenko, Mikhail Ya. Melnikov, Konstantin L. Ivanov, Ekaterina M. Budynina
Summary: A new method was developed for the design of diastereodivergent approach to phosphazenopyrrolines by switching step order within a cascade process. The strategy relies on the multifaceted roles of phosphazene intermediates in cascade transformation, providing a stereodivergent route to synthesize biorelevant compounds with different stereoisomers.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Food Science & Technology
Zhenhui Zhang, Lin Li, Yuting Li, Yi Wu, Xia Zhang, Haiping Qi, Bing Li
Summary: This study investigated the reactivity of o-benzoquinone with amino acids and N epsilon-(carboxymethyl) lysine (CML). The results showed that CML exhibited higher reactivity with o-benzoquinone compared to most amino acids. Even in complex systems, o-benzoquinone was still able to capture CML. Quantum chemistry predictions indicated that secondary amines have a greater reactivity with 4-methylbenzoquinone than primary amines with a similar molecular structure. Overall, o-benzoquinone has the potential to capture AGEs and reduce their harmful effects.
Article
Polymer Science
Jasmine Sinha, Shafer Soars, Christopher N. Bowman
Summary: This article describes an efficient enamine organocatalyzed thiol-Michael click reaction and its broad application in cross-linking polymerizations. The nucleophilicity of the enamines used is crucial for the reaction efficiency and overall yields, with in situ formation of an enamine via photo-deprotection of an amine showing promising results in facilitating thiol-Michael reactions and improving functional group conversion rates.
Article
Biochemistry & Molecular Biology
Hongchen Liu, Lei Guo, Yamin Dai, Mengya Li, Dongwei Wang, Yun Li, Haisong Qi
Summary: A cellulose-based hydrophobic paper was fabricated through surface chemical modification, which can be applied in various fields. The resulting paper showed good hydrophobic performance, high stability, and had no effect on the whiteness, writing, and printing properties of the paper. This paper construction strategy is simple, benign, and efficient.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Chemistry, Organic
Shibo Yu, Qihang Cai, Tianxu Yu, Jiahui Li, Chao Yao, Yue-Ming Li
Summary: This paper describes the design and application of new chiral ligands based on binaphthyl and proline skeletons, which incorporate regulatable electronic and steric properties for the imidazoline functional groups. These ligands form chiral complexes with different metal salts and can be used as catalysts for enantioselective conjugate addition reactions, resulting in high yields and excellent enantiomeric excess.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
S. Elakkiya, Velayutham Sudha, G. Sathya Priyadarshini, G. Selvi, Venkataraman Dharuman
Summary: In this study, a tripodal Schiff base compound was synthesized and its structure was confirmed using various techniques. The electrochemical sensing behavior of uric acid on a modified electrode was investigated, revealing high sensitivity, repeatability, and stability. Additionally, molecular docking studies showed strong binding affinity between the compound and Arthrobacter globiformis uricase.
INORGANIC CHEMISTRY COMMUNICATIONS
(2023)
Review
Chemistry, Multidisciplinary
Anastasia L. Gant Kanegusuku, Jennifer L. Roizen
Summary: Photomediated Giese reactions have become a forefront in radical chemistry, utilizing organometallic photocatalysts to generate carbon-centered radicals. Chemists have developed numerous strategies to access crucial carbon-centered radical intermediates for radical conjugate addition processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Kenya Tamaribuchi, Jiaqi Tian, Kengo Akagawa, Kazuaki Kudo
Summary: Enantioselective Michael addition of beta-dicarbonyl compounds towards nitroalkenes was achieved using an immobilized, N-terminal-guanidinylated peptide catalyst. Various nucleophiles and electrophiles were employed, with the resin-supported catalyst being recyclable for five cycles. This method shows promise for industrial applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
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
Chemistry, Multidisciplinary
Shannon L. Goes, Jordan E. Nutting, Nicholas J. Hill, Shannon S. Stahl, Mohammad Rafiee
Summary: This article describes the development of an undergraduate laboratory experience that introduces synthetic and analytical electrochemistry concepts to advanced organic chemistry students. The experiments provide an authentic experience in organic electrochemistry and strengthen fundamental organic chemistry skills.
JOURNAL OF CHEMICAL EDUCATION
(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
Buwanila T. Punchihewa, Vidit Minda, William G. Gutheil, Mohammad Rafiee
Summary: Electrochemistry plays a crucial role in chemical reactions and has wide applications in electroanalysis and electrosynthesis. By designing an electrochemical cell with a thin layer electrode, the limitations of traditional electrolysis cells can be bypassed, allowing for minute-scale electrolysis reactions and real-time probing of redox-active components.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
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
Chemistry, Multidisciplinary
Lida Khalafi, Nastaran Nikzad, Asayiel Alhajeri, Brandon Bacon, Karla Alvarado, Mohammad Rafiee
Summary: In this article, a demonstration and activity are presented to help students understand electrochemical phenomena by visualizing and analyzing the expansion of a micrometer-sized diffusion layer. The activity utilizes a kids' optical microscope with a digital eyepiece camera to observe and record the formation and expansion of the diffusion layer. By analyzing the time-dependent changes in the colorful diffusion layer, students can derive the diffusion coefficient of electrochemically generated hydroxide ion.
JOURNAL OF CHEMICAL EDUCATION
(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
Mohammad Rafiee, Dylan J. Abrams, Luana Cardinale, Zachary Goss, Antonio Romero-Arenas, Shannon S. Stahl
Summary: Electrochemical methods provide control over chemical synthesis by tuning the potential or current, and measuring the current or potential can offer mechanistic insights. This tutorial review explains the use of cyclic voltammetry and chronoamperometry to study reaction mechanisms, optimize electrochemical reactions, or design new reactions. These techniques allow analysis of concentrations of redox active species in solution and offer a versatile strategy for kinetic analysis.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Analytical
Mikayla N. Mayer, Mohammad Rafiee
Summary: In this study, insights from mechanistic studies on aminoxyl catalyzed oxidation of alcohols and aldehydes were utilized for the fabrication of a gas phase sensor for ethanol and acetaldehyde. This electrochemical sensor, composed of an aminoxyl radical and graphene oxide, can have its response and selectivity altered by tuning the basicity of the graphene oxide.
