Article
Chemistry, Organic
Mattis Damrath, Lucien D. Caspers, Daniel Duvinage, Boris J. Nachtsheim
Summary: Two simple methods for synthesizing O- and N-bridged diaryliodonium triflates are described. Different derivatizations were applied to demonstrate their usefulness as building blocks and to gain a deeper understanding of their general reactivity.
Article
Chemistry, Organic
Anze Zupanc, Marjan Jereb
Summary: This study presents the synthesis and characterization of N-iodo sulfoximines, with a one-pot cascade reaction yielding high isolated yields and demonstrating the iodination of aryls, oxidation, and conversion to N-SCF3 congeners.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Julien Borrel, Jerome Waser
Summary: In this study, a simplified synthesis method for generating Ethynylbenziodoxolones (EBXs) in one pot and directly applying them to substrate functionalization was reported. By bypassing the mandatory isolation and purification steps, this approach led to a more efficient synthesis and successful application in various transformations to obtain a diverse range of alkynylated products.
Article
Chemistry, Multidisciplinary
Tobias Michael Milzarek, Jerome Waser
Summary: The first trifluoromethylation of vinylbenziodoxolones (VBX) using bench-stable, high-valent copper(III) species is reported. The reaction can be initiated under thermal conditions and/or irradiation (365 nm) and leads to stereoselective formation of trifluoromethylated alkenes. Various VBX reagents derived from tyrosine, cysteine, small peptides, thiols, and amides can be used as precursors. The obtained alkenes can be further functionalized through reduction or epoxidation of the trifluoromethylated double bond. The method is suitable for large-scale batch/flow synthesis and can be conducted under visible light irradiation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Nagaraju Sakkani, Dhiraj Kumar Jha, Nouraan Sadiq, John C. -G. Zhao
Summary: A one-pot alkylation-aminoxidation reaction of styrene derivatives was achieved by in situ-generated alkyl and N-oxyl radicals. The corresponding O-alkylated hydroxylamine derivatives were obtained in moderate to good yields. The reaction involves the use of phenyliodine(iii) dicarboxylates for the generation of alkyl radicals and oxidants for N-oxyl radicals, along with the first generation of beta-enaminyl radicals through a HAT process and their use as single-electron donors.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Lachlan Barwise, Jason D. Bennetts, Keith F. White, Jason L. Dutton
Summary: The synthesis and crystallographic characterization of NO2-C6H4-I(NTf2)(2) (NTf2 = bistriflimide) are reported. Experimental results demonstrate that this compound is capable of performing oxidation reactions that ArI(OTf)2 is unable to. Theoretical analysis indicates that Ar-I(NTf2)(2) is the most oxidizing compound among the known ArIL2 class of compounds, and it may also be the most oxidizing compound among the practically possible compounds in this class.
CHEMICAL COMMUNICATIONS
(2023)
Article
Multidisciplinary Sciences
Yuanting Cai, Yuhui Hua, Zhengyu Lu, Qing Lan, Zuzhang Lin, Jiawei Fei, Zhixin Chen, Hong Zhang, Haiping Xia
Summary: This study demonstrates successful electrophilic aromatic substitution (EAS) reactions of molecules with Craig-Mobius aromaticity, such as osmapentalenes and fused osmapentalenes, which exhibit high reactivity to halogen electrophilic attack. Additionally, selective formation of a series of halogen-substituted metalla-aromatics via EAS reactions reveals a novel approach to otherwise elusive compounds. Density functional theory calculations were utilized to study the electronic effect on the regioselectivity of the EAS reactions.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2021)
Article
Chemistry, Organic
Saibal Sar, Ranajit Das, Dhiraj Barman, Pikaso Latua, Souvik Guha, Ludovic Gremaud, Subhabrata Sen
Summary: In this study, pyrrole and indole derivatives were functionalized using the dimethyl malonate derived phenyl iodonium ylide 4a in the presence of a blue LED in methanol, resulting in the desired compounds. Control experiments provided insight into the probable reaction mechanism, and the strategy was successfully applied in the generation of other compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Chenyang Wang, Peng Shi, Carsten Bolm
Summary: In this study, dichloro- and dibromomethane were utilized as halogen sources to convert NH-sulfoximines to N-halo derivatives, using an in situ formed sulfoximidoyl-containing hypervalent iodine reagent under visible light. The reactions were carried out in air without the need for catalysts or additives, and the products were obtained in good to excellent yields.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Di Wu, Chengcheng Li, Yongjie Duan, Hongquan Yin, Fu-Xue Chen
Summary: In this study, a chlorothiocyanato difunctionalization reaction was achieved, and various alpha-chlorothio/selenocyanato difunctional ketones were synthesized through a one-pot strategy from beta-keto acids. The high yield and wide scope of substrates make this approach more practical for the synthesis of alpha-substituented difunctional ketones.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Chenyang Wang, Yongliang Tu, Ding Ma, Chaimae Ait Tarint, Carsten Bolm
Summary: The reaction between [Bis(difluoroacetoxy)iodo]benzene and NH-sulfoximines produces hypervalent iodine(III) reagents, which can transfer difluoroacetoxy and sulfoximidoyl groups to styrenes with high regioselectivity under photocatalysis. Mechanistic investigations suggest the involvement of radicals and highlight the importance of the difluoroacetoxy group in the iodine reagent.
Article
Chemistry, Organic
Wen Liu, Shuya Xing, Shao-Fei Ni, Cheng Ma, Qiujin Fan, Zhiyong Ye, Yanchuang Zhao, Ting Ouyang, Ying Bai, Xinxin Shao
Summary: In this research, a Lewis base-catalyzed trifluoromethylsulfinylation of alkyl alcohols and phenols was achieved using a stable electrophilic trifluoromethylsulfinylating reagent, resulting in the modular synthesis of various trifluoromethanesulfinate esters. This metal-free and catalytic transformation displayed broad functional group compatibility, enabling the late-stage modification of complex molecules and allowing the reuse of the phthalimide reagent. Notably, the reaction of 1-indanol led to the formation of alkenes, suggesting an intriguing mechanistic pathway involving O-trifluoromethylsulfinylation and subsequent elimination.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Arianna Tota, Marco Colella, Claudia Carlucci, Andrea Aramini, Guy Clarkson, Leonardo Degennaro, James A. Bull, Renzo Luisi
Summary: A new method for synthesizing hydrazinium salts under mild and simple conditions, tolerant to other functional groups including bioactive molecules, was reported. Insights on the structure of hydrazinium salts were provided by X-ray analysis.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Lipiao Bao, Baolin Zhao, Bowen Yang, Marcus Halik, Frank Hauke, Andreas Hirsch
Summary: A series of hypervalent iodine compounds have been reported as highly efficient for diversified graphene patterning, generating reactive radicals for controlled chlorination, hydroxylation, and trifluoromethylation. The highly functionalized graphene nanoarchitectures allow for reversible attachment of functional entities with full control over stored chemical information. This work provides an exciting approach for target 2D functionalization and modulation of graphene using suitable hypervalent iodine compounds.
ADVANCED MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Huaiyuan Zhang, Thomas Wirth
Summary: Xanthene derivatives derived from BINOL have wide applications in various fields such as medicine, fluorescent probes, dyes, and food additives. Researchers have developed synthetic methods for preparing the oxidized products of BINOL using different methods. One-pot reactions of BINOLs, reagents, and nucleophiles have also been investigated, resulting in high-yielding products.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Chemistry, Multidisciplinary
Simon L. Roessler, Benson J. Jelier, Emmanuel Magnier, Guillaume Dagousset, Erick M. Carreira, Antonio Togni
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Kosuke Higashida, Fabian Bruning, Nagataka Tsujimoto, Kenya Higashihara, Haruki Nagae, Antonio Togni, Kazushi Mashima
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Pascal S. Engl, Alexey Tsygankov, Jordan Silva, Jean-Paul Lange, Christophe Coperet, Antonio Togni, Alexey Fedorov
HELVETICA CHIMICA ACTA
(2020)
Editorial Material
Chemistry, Multidisciplinary
Antonio Togni
Article
Chemistry, Multidisciplinary
Dustin Bornemann, Cody Ross Pitts, Lionel Wettstein, Fabian Bruning, Sebastian Kung, Liangyu Guan, Nils Trapp, Hansjorg Grutzmacher, Antonio Togni
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Physical
Kheironnesae Rahimidashaghoul, Iveta Klimankova, Martin Hubalek, Vaclav Matousek, Josef Filgas, Petr Slavicek, Tomas Slanina, Petr Beier
Summary: The study utilized different reagents for fluoroalkylation, with the photochemical process showing better selectivity. However, side reactions still occurred in the presence of cysteine residues.
Article
Chemistry, Multidisciplinary
Jorna Kalim, Thibaut Duhail, Ewa Pietrasiak, Elsa Anselmi, Emmanuel Magnier, Antonio Togni
Summary: A study has discovered a method for direct trifluoromethylation of various aliphatic alcohols using a hypervalent iodosulfoximine reagent, resulting in the efficient synthesis of corresponding ethers.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Phil Liebing, Cody Ross Pitts, Marc Reimann, Nils Trapp, David Rombach, Dustin Bornemann, Martin Kaupp, Antonio Togni
Summary: The analysis of crystal structures of SF5- or SF4-containing molecules showed that these groups are often surrounded by hydrogen or other fluorine atoms, and F...F contacts are important in many compounds. Additionally, repeating structural motifs formed by contacts between SF5 groups were identified, including different supramolecular dimers and infinite chains.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Markus T. Mueller, Antonio Togni, Carlo Thilgen
Summary: ETH Zurich evaluated the basic chemistry knowledge of first-year students in Chemistry, Biology, Pharmaceutical Sciences, and Health Sciences and Technology disciplines, finding that some students performed better than others, with no significant differences observed between gender or region.
Article
Chemistry, Inorganic & Nuclear
Hyunchul Kwon, Ewa Pietrasiak, Takashi Ohhara, Akiko Nakao, Boknam Chae, Chan-Cuk Hwang, Daesung Jung, In-Chul Hwang, Young Ho Ko, Kimoon Kim, Eunsung Lee
Summary: The synthesis of sandwich-shaped multinuclear silver complexes with planar penta- and tetranuclear wheel-shaped silver units and a central anion is reported. By altering the central anion or adding/removing a silver atom, the size of the silver wheels can be adjusted. NMR mechanistic studies reveal the formation sequence of the silver complexes and provide insights into the dynamics of the self-assembly process.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hwi Yul Jo, Jeong Min Lee, Ewa Pietrasiak, Eunsung Lee, Young Ho Rhee, Jaiwook Park
Summary: A new method for synthesizing N-H imines efficiently has been developed, with high yields of the products. Furthermore, the N-H imines can react with specific amines to form stable compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Daniel Abegg, Martin Tomanik, Nan Qiu, Dany Pechalrieu, Anton Shuster, Bruno Commare, Antonio Togni, Seth B. Herzon, Alexander Adibekian
Summary: The tetrafluoroalkyl benziodoxole (TFBX) has emerged as a powerful cysteine-selective chemoproteomic probe, featuring superior target occupancy, faster labeling kinetics, and broader proteomic coverage compared to traditional cysteine-reactive probes. This new probe has been demonstrated to successfully identify cellular targets of (-)-myrocin G, leading to the discovery of the first reported inhibitors of the biomedically important protein XRCC5. Additionally, this probe disrupts the interaction of XRCC5 with DNA, sensitizing cancer cells to chemotherapeutic agents and UV-light-induced DNA damage.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
Yannick Kraemer, Emily Nicole Bergman, Antonio Togni, Cody Ross Pitts
Summary: In the development of synthetic methods, researchers discovered a mild and inexpensive oxidative fluorination method based on potassium fluoride and trichloroisocyanuric acid (TCICA), which enabled the synthesis of pentafluorosulfanyl (SF5) compounds. Further exploration led to the discovery of its application in the synthesis of other fluorinated heteroatoms. Ultimately, it was found that this method can be used to synthesize SF5Cl.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Ewa Pietrasiak, Christopher P. Gordon, Christophe Coperet, Antonio Togni
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2020)
