Article
Chemistry, Multidisciplinary
Kumar Bhaskar Pal, Ester Maria Di Tommaso, A. Ken Inge, Berit Olofsson
Summary: We report an efficient radical-mediated C-C coupling through photoredox-catalyzed reactions of 4-alkyl-dihydropyridines (DHPs) and vinylbenziodoxol(on)es (VBX, VBO). This transition-metal-free and mild photocatalytic method has excellent functional group tolerance and affords vinylated products in good yields, with complete retention of the alkene configuration. The utility of the methodology is demonstrated by the diastereoselective synthesis of C-vinyl glycosides. Preliminary mechanistic studies suggest that the C-C bond formation is stereospecific and proceeds through a concerted radical coupling transition state.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jessica C. Bieniek, Boris Mashtakov, Dieter Schollmeyer, Siegfried R. Waldvogel
Summary: This study presents an electrocatalytic method using hypervalent iodine(III) as a mediator to synthesize 1H-N-aryl-3,4-dihydroquinolin-2-ones by C-N bond formation. The method features a low catalyst loading, recycling of the solvent, and is a sustainable alternative to conventional approaches.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Physical
Nelly F. Nunheim, Werner R. Thiel
Summary: Systematic optimization of the Ru-catalyzed oxidation of alcohols using TBHP as the oxidizing agent was carried out. A sustainable protocol was developed using a water/tert-butanol mixture as the solvent and a syringe pump for continuous addition of the oxidizing agent, resulting in high yields and selectivity.
Article
Chemistry, Multidisciplinary
Yuan-Yuan Xu, Zhong-Hua Gao, Cao-Bo Li, Song Ye
Summary: The enantioselective alpha-oxidative coupling of enals with carboxylic acids was achieved by umpolung of an NHC-bound enolate with an iodine(III) reagent. The reaction produced alpha-acyloxyl-beta,gamma-unsaturated esters in good yields, with high regio- and enantioselectivities. The reaction involved the formation of an enol iodine(III) intermediate from the enolate with iodosobenzene, which changed the polarity of the enal's alpha-carbon from nucleophilic to electrophilic and facilitated the subsequent carboxylate addition.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Aaron G. Nash, Colton J. Breyer, Brett D. Vincenzini, Gregory I. Elliott, Jens Niklas, Oleg G. Poluektov, Arnold L. Rheingold, Diane K. Smith, Djamaladdin G. Musaev, Douglas B. Grotjahn
Summary: This study reports a catalyst that maintains high electrocatalytic turnover frequency at very low pH values, with high current densities and excellent durability. Preliminary computational studies suggest that the sulfonate group in the active site acts as a proton relay even in strong acid.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Sakshi Soni, Rimi, Vinod Kumar, Kotaro Kikushima, Toshifumi Dohi, Viktor V. Zhdankin, Ravi Kumar
Summary: The chemistry of hypervalent iodine compounds, both as stoichiometric reagents and catalysts, has been extensively studied in recent decades. Hypervalent iodine (V)-catalyzed reactions have proven to be versatile systems for various oxidative transformations. This review discusses the versatility of hypervalent iodine (V)-catalyzed reactions in detail, highlighting the oxidation of various substrates using catalytic amounts of o-iodoxybenzoic acid, modified IBX derivatives, o-iodoxybenzenesulfonic acid, recyclable iodine (V), and non-cyclic/pseudocyclic iodine (V) compounds.
Article
Chemistry, Multidisciplinary
Bing Zu, Jie Ke, Yonghong Guo, Chuan He
Summary: Anodic oxidation enables the synthesis and derivatization of hypervalent iodine(III) reagents from aryl iodides under mild electrochemical conditions. This method offers a straightforward and sustainable approach by using only electrons as the oxidation reagents, thus avoiding the use of expensive or hazardous chemical oxidants.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Applied
Erika Linde, Shobhan Mondal, Berit Olofsson
Summary: Our group has developed new methods for the synthesis of diaryliodonium salts, which are versatile reagents in organic synthesis and materials chemistry. We have identified limitations in the existing protocols for synthesizing different types of diaryliodonium salts. In this update, we discuss the challenges related to the stability and reactivity of the reagents and propose strategies to overcome these limitations.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Editorial Material
Chemistry, Multidisciplinary
Avijit Roy, Martin Oestreich
Summary: For a long time, the Me3Si group has been difficult to manipulate into another useful functional group, but a hypervalent iodine reagent has now been shown to achieve electrophilic demethylation for this purpose. Coupled with the Tamao-Fleming oxidation, the Me3Si group can serve as a placeholder for a hydroxy group.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Chandan Chaudhari, Katsutoshi Sato, Shin-ichiro Miyahara, Tomokazu Yamamoto, Takaaki Toriyama, Syo Matsumura, Kohei Kusuda, Hiroshi Kitagawa, Katsutoshi Nagaoka
Summary: Supported Ru catalysts prepared from different Ru precursors were used for the hydrogenation of benzaldehyde, resulting in high yield of benzyl alcohol. The catalyst exhibited moderate acidic and basic nature, which was favorable for controlling the selectivity of benzyl alcohol. Highly dispersed Ru nanoparticles showed effective performance for the hydrogenation of benzaldehyde. The Ru-CO/HT catalyst demonstrated good tolerance towards different functional groups and maintained stability until the 7th recycling cycle.
Article
Chemistry, Organic
Julian Spils, Thomas Wirth, Boris J. Nachtsheim
Summary: We present a multi-step continuous-flow approach to produce six-membered diaryliodonium salts, with improved scalability and atom economy compared to existing batch methods. Benzyl acetates serve as readily available and cost-effective starting materials in this two-step procedure. An acid-catalyzed Friedel-Crafts alkylation followed by an anodic oxidative cyclization results in a defined set of cyclic iodonium salts, with yield depending on the substrate characteristics.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Preeti Devi, Muthukumar Kannan, Kiran, Virender, Ashwani Kumar, Senthilkumar Muthaiah
Summary: A highly efficient oxidation of secondary alcohols has been achieved using three different in situ catalyst systems, all of which are environmentally friendly and highly atom economical. These catalyst systems were generated from commercially available ruthenium(II)benzenedichloride dimer, dichloro(1,5-cyclooctadiene)ruthenium(II) polymer, and ruthenium(II)(p-cymene)dichloride dimer, in combination with the additive hexamethylenetetramine. The catalyst systems showed high activity even at low catalyst loadings, and the oxidation reactions proceeded via a dehydrogenative pathway to produce hydrogen as the sole product. The developed catalyst systems have potential applications in the release of hydrogen from liquid organic hydrogen carriers.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Review
Chemistry, Organic
Diogo L. Poeira, Maria Manuel B. Marques, Ana Claudia R. Negrao, Joao Macara
Summary: In recent years, there has been a significant increase in the number of protocols for alpha-amination of carbonyl compounds, emphasizing the importance of this functional group. While classical approaches are still being used, new methods with unique advantages, such as the use of umpoled enolates, generation of electrophilic nitrogen sources, and oxidative methods, have also emerged.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jully Patel, Gabriel Bury, Alireza K. Ravari, Roman Ezhov, Yulia Pushkar
Summary: This study investigates the descriptors correlated with catalytic activity through the synthesis and characterization of two catalysts. The results show that the introduction of an ethoxy group can enhance the catalytic activity in chemically driven and photocatalytic water oxidation, and it is related to the configuration of the Ru-oxo unit.
Article
Chemistry, Multidisciplinary
Michael Schaefer, Timo Stuenkel, Constantin G. Daniliuc, Ryan Gilmour
Summary: The regio- and enantioselective intermolecular vicinal fluoroamination of alpha-trifluoromethyl styrenes has been achieved through enantioselective I-I/I-III catalysis, providing facile access to tertiary benzylic stereocenters bearing both CF3 and F groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Akira Yoshimura, Michael T. Shea, Cody L. Makitalo, Melissa E. Jarvi, Gregory T. Rohde, Akio Saito, Mekhman S. Yusubov, Viktor V. Zhdankin
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Hisato Shimizu, Akira Yoshimura, Keiichi Noguchi, Victor N. Nemykin, Viktor V. Zhdankin, Akio Saito
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Irina A. Mironova, Pavel S. Postnikov, Rosa Y. Yusubova, Akira Yoshimura, Thomas Wirth, Viktor V. Zhdankin, Victor N. Nemykin, Mekhman S. Yusubov
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Review
Chemistry, Multidisciplinary
Akira Yoshimura, Akio Saito, Viktor V. Zhdankin
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Organic
Mekhman S. Yusubov, Natalia S. Soldatova, Pavel S. Postnikov, Rashid R. Valiev, Dmitry Y. Svitich, Roza Y. Yusubova, Akira Yoshimura, Thomas Wirth, Viktor V. Zhdankin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Correction
Chemistry, Organic
Nicolai Dieltiens, Diederica D. Claeys, Viktor V. Zhdankin, Victor N. Nemykin, Bart Allaert, Francis Verpoort, Christian V. Stevens
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Akira Yoshimura, Michael T. Shea, Olga Guselnikova, Pavel S. Postnikov, Gregory T. Rohde, Akio Saito, Mekhman S. Yusubov, Victor N. Nemykin, Viktor V. Zhdankin
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Zhargolma B. Bazarova, Ludmila S. Soroka, Alex A. Lyapkov, Mekhman S. Yusubov, Francis Verpoort
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Natalia S. Soldatova, Pavel S. Postnikov, Mekhman S. Yusubov, Thomas Wirth
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Biochemistry & Molecular Biology
Akira Yoshimura, Cody L. Makitalo, Melissa E. Jarvi, Michael T. Shea, Pavel S. Postnikov, Gregory T. Rohde, Viktor V. Zhdankin, Akio Saito, Mekhman S. Yusubov
Review
Chemistry, Organic
Akira Yoshimura, Akio Saito, Mekhman S. Yusubov, Viktor V. Zhdankin
SYNTHESIS-STUTTGART
(2020)
Article
Biochemistry & Molecular Biology
Michael T. Shea, Gregory T. Rohde, Yulia A. Vlasenko, Pavel S. Postnikov, Mekhman S. Yusubov, Viktor V. Zhdankin, Akio Saito, Akira Yoshimura
Summary: Hypervalent iodine heterocycles are an important class of reagents in organic synthesis, and this paper presents a simple and convenient method for the synthesis of benziodazolones using readily available iodobenzamides and m-chloroperoxybenzoic acid. The new iodine heterocycles were confirmed by X-ray analysis and shown to react more efficiently than analogous benziodoxolone reagents in esterification reactions.
Article
Biochemistry & Molecular Biology
Irina A. Mironova, Valentine G. Nenajdenko, Pavel S. Postnikov, Akio Saito, Mekhman S. Yusubov, Akira Yoshimura
Summary: The intramolecular oxidative cycloaddition reaction of alkyne- or alkene-tethered aldoximes was efficiently catalyzed by hypervalent iodine(III) species, resulting in the formation of polycyclic isoxazole derivatives with yields of up to 94%. The structure of the products was confirmed through various methods, including X-ray crystallography. Mechanistic studies revealed the critical role of hydroxy(aryl)iodonium tosylate as a precatalyst, which is formed from 2-iodobenzoic acid and m-chloroperoxybenzoic acid in the presence of a catalytic amount of p-toluenesulfonic acid.
Review
Biochemistry & Molecular Biology
Stanislav A. Petrov, Mekhman S. Yusubov, Elena K. Beloglazkina, Valentine G. Nenajdenko
Summary: This review presents the progress made in the synthesis of radioiodinated compounds over the past decade. It discusses the possibilities and limitations of radiopharmaceuticals with different iodine isotopes, as well as the synthesis of low and high molecular weight compounds containing radioiodine. The review also analyzes synthesis strategies, substrate frameworks, isolation methods, and metabolic stability, and explores the potential for industrial production of radioiodinated organic derivatives for drug synthesis and diagnostics.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Organic
Natalia S. Soldatova, Pavel S. Postnikov, VitaIli V. Suslonov, Troyana Yu Kissler, Daniil M. Ivanov, Mekhman S. Yusubov, Bartomeu Galmes, Antonio Frontera, Vadim Yu Kukushkin
ORGANIC CHEMISTRY FRONTIERS
(2020)
