Article
Chemistry, Organic
Michael P. Stanton, Jessica M. Hoover
Summary: A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method provides alkenes from carboxylic acids without the need for stoichiometric Pb or Ag additives or expensive or specialized photocatalysts. Mechanistic experiments show that the reaction proceeds via benzylic deprotonation and subsequent radical decarboxylation, which is different from the single electron-transfer mechanisms in related reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Noah Jeremias, Lisa-Marie Mohr, Thorsten Bach
Summary: 2-Aryl-1-sulfonyl-substituted cyclobutanes were synthesized via an intermolecular [2 + 2] photocycloaddition using various alpha,beta-unsaturated sulfones and olefins. Lewis acids were employed to catalyze this reaction, with chiral-at-metal Lewis acid achieving enantioselective outcomes up to 77% ee.
Review
Food Science & Technology
Michael N. Clifford, Laurence J. King, Asimina Kerimi, Maria Gema Pereira-Caro, Gary Williamson
Summary: This review discusses the modulation of gut microbiota and endogenous beta-oxidation by phenyl-ring substitution and flux in omega-phenyl-alkenoic acids. Different types of omega-phenyl-alkenoic acids have different metabolic pathways and substrate characteristics, which may be related to limited pools of coenzyme A and metabolic regulation in the body.
CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION
(2022)
Article
Chemistry, Multidisciplinary
Weiming Chen, Xin Xie, Jian Zhang, Jian Qu, Can Luo, Yaozhu Lai, Feng Jiang, Han Yu, Yongge Wei
Summary: An efficient method for the carbon-carbon bond cleavage of 1,2-diols using an iron catalyst in acetic acid with hydrogen peroxide as the oxidant was reported. The method showed high conversion rate and selectivity, and was also efficient in degrading renewable biomass oleic acid.
Review
Chemistry, Organic
Indrapal Singh Aidhen, Sriranjani Srikanth, Heera Lal
Summary: This review provides a brief overview of important dietary phenolics and their biological properties, serving as a guide for ongoing research in therapeutics.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yi-Min Jiang, Yi Yu, Shao-Fen Wu, Hong Yan, Yaofeng Yuan, Ke-Yin Ye
Summary: An environmentally friendly and efficient electrochemical method has been developed for the synthesis of beta-fluorosulfones from styrenes using sulfonylhydrazides and triethylamine trihydrofluoride. The reaction conditions are mild and have a broad substrate scope, easily scalable to gram-scale preparation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Liangkun Pan, Long Zheng, Ye Chen, Zhihai Ke, Ying-Yeung Yeung
Summary: A mechanochemical method using hypervalent iodine reagents has been developed for the functionalization of olefins, enabling the synthesis of 1,3-dioxygenated compounds. Under similar reaction conditions with the addition of molecular iodine, 1,4-iodoalcohols can also be synthesized. These valuable products are difficult to achieve using traditional solution-phase methods. Mechanistic study suggests that the hypervalent iodine reagent may dimerize at the solid state and trigger the 1,3- and 1,4-difunctionalization reactions in an intermolecular cascade manner.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Medicinal
Francesco Melfi, Simone Carradori, Noemi Mencarelli, Cristina Campestre, Marialucia Gallorini, Silvia Di Giacomo, Antonella Di Sotto
Summary: This article provides a brief description of the anticancer potential of natural compounds, followed by a search for patents published from 2019 onwards according to the PRISMA guidelines. Additionally, relevant publications from the overall scientific literature were discussed.
EXPERT OPINION ON THERAPEUTIC PATENTS
(2023)
Article
Chemistry, Organic
Takehiro Kato, Yuya Okada, Yuto Fujii, Muhammet Uyanik, Kazuaki Ishihara
Summary: The reported method is a practical and environmentally friendly approach for the oxidative Ritter-type chloroamidation of alkenes using sodium chloride and oxone in acetonitrile under mild conditions. The reaction shows excellent chemoselectivity and can be easily scaled up for synthesis. No catalyst is needed for this non-aqueous reaction.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Valentina Bertolini, Rebecca Appiani, Marco Pallavicini, Cristiano Bolchi
Summary: Treatment of cyclic ketones with Oxone in 1M NaH2PO4/Na2HPO4 water solution can efficiently and quantitatively convert them into 5-, 6-, and 7-membered lactones, important synthons, without the formation of hydroxyacids. This green and simple method eliminates the need for more complex and non-eco-friendly procedures previously developed to avoid lactone hydrolysis, and can also be applied to water-insoluble ketones.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Boris G. Ershov, Nadezhda M. Panich, Gennadii L. Bykov, Alexander L. Kustov, Vladimir G. Krasovskiy, Leonid M. Kustov
Summary: Ozonolysis is used to oxidize a model cyclic molecule-decalin, achieving a conversion rate exceeding 50% with the main products being carboxylic acids. Through various spectroscopic methods, it is revealed that the key stage of the reaction involves the activation of the first C-H bond and the formation of peroxide radicals.
Review
Chemistry, Multidisciplinary
Shi-Hui Shi, Yujie Liang, Ning Jiao
Summary: Selective C-C bond cleavage using electrochemical methods has been identified as a sustainable and scalable strategy that shows potential in replacing chemical reagents with electricity. Progress in this area has been made, with more examples of C-C bond cleavage via different maneuvers being developed recently, showcasing the exciting potential of electrochemical synthesis.
Article
Chemistry, Applied
Haiyan Li, Yunxiang Ma, Xudong Gao, Guopeng Chen, Zhipeng Wang
Summary: In this study, four cinnamic acids were used to modify porous starch with esterification, confirming the ester linkage through various analyses. The modified starch maintained its porous structure, and exhibited different antioxidant capacities in vitro, with SA@PS showing the highest antioxidant activity due to the presence of phenolic hydroxyl groups. This research not only investigated the antioxidant mechanism of these modified starch derivatives but also provided insights for the synthesis of biodegradable antioxidant materials for the food industries.
CARBOHYDRATE POLYMERS
(2021)
Article
Forestry
Andrey N. Evdokimov, Alexander Kurzin, Larisa M. Popova, Victorija B. Franchuk
Summary: Tall oil fatty acids contain rosin acids and stilbenes as impurities, with the latter causing color deterioration. Current methods for removing stilbenes involve using sorbents, formaldehyde, and boron trifluoride etherate, with phosphorus pentoxide treatment being effective in reducing pinosylvin ethers content.
EUROPEAN JOURNAL OF WOOD AND WOOD PRODUCTS
(2021)
Article
Engineering, Environmental
Hiu Lam So, Wei Chu, Weicheng Xu
Summary: Naphthalene degradation was successfully achieved using graphene/oxidized graphene/UV photocatalysis. The reaction is influenced by catalysis and adsorption mechanisms under acidic and alkaline conditions, with improved performance observed after reuse.
JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING
(2021)
Article
Chemistry, Multidisciplinary
Soumen Payra, Navin Yadav, Jarugu Narasimha Moorthy
Summary: This study investigated the reaction pathways of aryl olefins and thiols in the presence of Oxone in different solvent systems, revealing two distinct reaction pathways leading to the synthesis of two different products.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kanyashree Jana, Jarugu Narasimha Moorthy
Summary: The spatial disposition of three benzene rings in triptycene allows for 'homoconjugation', a contentious issue in the literature. Through the design and synthesis of a diagnostic photochromic molecular system, the persistence of a photogenerated colored o-quinonoid intermediate supports the operation of homoconjugation.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Keshaba N. Parida, Jarugu Narasimha Moorthy
Summary: This article introduces the development of improved IBX with enhanced solubility and reactivity in organic solvents. The design principles to eliminate the explosive attributes by manipulating the structure of IBX are discussed. A convenient oxidative transformation method using Oxone (R) catalyst is presented, and the applications of improved IBX in efficient oxidations are summarized.
Article
Chemistry, Multidisciplinary
Parag Tamuly, Farasha Sama, Jarugu Narasimha Moorthy
Summary: A layered metal-organic framework (MOF), Cd-BPDP, was synthesized using a metal-assisted self-assembly method. The MOF was then exfoliated into porous 2D metal-organic nanosheets (MONs) through ultrasonication and mechanical grinding techniques. The resulting MONs showed significant iodine capture ability, attributed to the increased surface area, charge-transfer complex formation, and reinforced binding of iodine through charge transfer.
ADVANCED MATERIALS INTERFACES
(2022)
Article
Chemistry, Organic
Navin Yadav, Soumen Payra, Jarugu Narasimha Moorthy
Summary: A metal-free and green iodine-catalyzed protocol is described for the synthesis of unsymmetrical thiosulfonates. The reactions occur at room temperature and provide good-to-excellent yields of the desired products.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Chetna Yadav, Ajay Kumar Sahoo, Jarugu Narasimha Moorthy
Summary: In this study, two porous organic polymers (POPs) were synthesized and used to stabilize metal nanoparticles. By embedding metal nanoparticles into the POPs, recyclable catalysts were achieved, and it was also demonstrated that the POPs exhibited high selectivity for adsorbing clean fuel, hydrogen gas.
ACS APPLIED NANO MATERIALS
(2022)
Article
Chemistry, Multidisciplinary
Kanyashree Jana, Jarugu Narasimha Moorthy
Summary: Regioisomeric naphthopyrans annulated with triptycene, Prox-NP and Dist-NP, exhibit different photochromic behaviors. Prox-NP produces a stable colored intermediate, Prox-NPQ, while Dist-NP does not. The rigid triptycene scaffold of Prox-NP leads to higher constraint and stability.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Keshaba N. N. Parida, J. Narasimha Moorthy
Summary: Hypervalent iodine (III and V) compounds undergo positional isomerization via pseudorotation or twisting. By using steric hindrance, the twisting process can be facilitated to promote reactivity. Ortho-substitution in iodanes accelerates the alpha-tosyloxylation of ketones and oxidation of alcohols. The enhanced reactivity is a result of non-planarity induced by steric hindrance and the weakening of the 3c-4e bonds involving the hypervalent iodine atom. Ortho-substitution is an important strategy to control reactivity, selectivity, and develop new catalysts for various reactions. This review covers the literature developments on the effect of substituents and twisting/pseudorotation on the stability and reactivity of hypervalent iodanes and their application in synthetic transformations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Kanyashree Jana, Debarghya Sarkar, Preeti Jaiswal, Jarugu Narasimha Moorthy
Summary: A set of donor-acceptor azahelical coumarins (DA-AHCs) with high fluorosolvatochromic shifts and high quantum yields in solution and solid states were designed and synthesized. The excited-state properties of these compounds were investigated, revealing the contribution of intramolecular charge transfer and crystal packing to their emission behaviors. The analysis showed that strengthened hydrogen bonding promoted quenching, efficient crystal packing promoted high emission, and loose crystal packing contributed to excited-state deactivation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Navin Yadav, Sushil Ranjan Bhatta, Jarugu Narasimha Moorthy
Summary: This study demonstrates a visible light-mediated synthesis of hetero-arenes (isoquinolines, benzothiazoles, and quinazolines) through the use of isocyanides and inexpensive acyl peroxides. It is the first time that singlet-excited isocyanides have been shown to decompose acyl peroxides into aryl/alkyl radicals. The resulting radicals attack isocyanides, leading to the formation of imidoyl radicals which subsequently cyclize to generate heteroarene products. The protocol eliminates the need for external photocatalysts, oxidants, additives, and bases.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Alka Karn, Chetna Yadav, Ajay Kumar Sahoo, Jarugu Narasimha Moorthy
Summary: A porous organic polymer (POP) with carboxylic acid functionalities, known as Carboxy-POP, has been developed for efficient heterogeneous catalytic reactions. The catalyst exhibits high catalytic activity, easy operation, high yields, short reaction times, and good recyclability.
Article
Chemistry, Organic
Ajeet Chandra, Navin Yadav, Soumen Payra, Keshaba N. Parida
Summary: o-Iodoxybenzoic acid (IBX) and Dess-Martinperiodinane (DMP) are effective in converting thiol to thiosulfonate at room temperature. DMP shows superior reaction rate, conversion, and equivalents compared to IBX. IBX oxidation of benzyl thiols results in thiosulfonates, while DMP produces O-benzylesters. The one-pot conversion of a thiol to an ester is unprecedented and holds potential for functional group transformations.
Article
Chemistry, Organic
Navin Yadav, Soumen Payra, Parag Tamuly, Jarugu Narasimha Moorthy
Summary: In this study, the synthesis of beta-hydroxysulfones instead of beta-ketosulfones was selectively demonstrated using dye-sensitized photocatalysis. The reaction utilized inexpensive and readily available olefins and sulfonyl hydrazides/N-hydroxy sulfonamides in the presence of oxygen. It was found that the hydroxysulfonylation reaction, which employed rose bengal as a photocatalyst and dioxygen as an oxidant, selectively produced secondary and tertiary beta-hydroxysulfones in good yields. The formation of beta-hydroxysulfones and beta-ketosulfones was shown to proceed through different routes depending on the concentration of oxygen.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Organic
Tarek H. El-Assaad, Jayden Zhu, Anjitha Sebastian, Dominic McGrath, Ishita Neogi, Keshaba N. Parida
Summary: Dioxiranes are versatile reagents with mild and selective oxygen transfer properties, capable of various transformations such as oxidations, epoxidations, and C-H hydroxylation. They find wide applications in the synthesis of natural products, drugs, and biomolecules.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
