Article
Chemistry, Physical
Cayo Lee, Alina J. Cook, Jonathan E. Elisabeth, Nathan C. Friede, Glenn M. Sammis, Nicholas D. Ball
Summary: In the past decade, there has been remarkable growth in catalytic transformations in organic sulfur(VI) fluoride chemistry. This article focuses on foundational examples utilizing catalytic strategies to synthesize and react S(VI) fluorides, with an emphasis on key mechanistic studies aimed at providing insight for future catalytic systems.
Article
Chemistry, Multidisciplinary
Dmytro Kravchuk, Tori Z. Forbes
Summary: A solvent-free synthetic pathway to uranyl triperoxide solids was demonstrated by reacting uranium trioxide with solid metal peroxides, resulting in the formation of crystalline uranyl triperoxide phases, m(30)-UO3-Li2O2 and m(15)-UO3-Na2O2.
Article
Biochemistry & Molecular Biology
Esko Salojarvi, Anssi Peuronen, Narhari Sapkota, Ari Lehtonen
Summary: Molecular molybdenum complexes with sulfur donor ligands are studied as model compounds for molybdenum enzymes, showing a stable Mo(IV) complex after reaction with thionation reagent. The complexes retain the original geometry, despite formally being Mo(IV) systems.
Article
Chemistry, Organic
James A. Vogel, Rania Hammami, Ara Ko, Hiya Datta, Yael N. Eiben, Karley J. Labenne, Ellis C. McCarver, Ebrar Z. Yilmaz, Patrick R. Melvin
Summary: We report the synthesis of sulfone iminium fluorides (SIFs), a reactive class of sulfur(VI) molecules. The synthesis is tolerant of various substituents and can be used for deoxyfluorination of alcohols and carboxylic acids, as well as in sulfur fluoride exchange (SuFEx) reactions. The products obtained from these reactions show high yields and short reaction times.
Article
Chemistry, Organic
Twinkle I. Patel, Ramkrishna Laha, Matthew J. Moschitto
Summary: In this study, a selective method for the synthesis of C2-substituted sulfones using sodium tert-butyldimethyl silyloxymethylsulfinate and quinoline N-oxides was reported. This scalable transformation has broad applicability to various quinoline and isoquinoline functionalities.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
P. Scott Pedersen, David C. Blakemore, Gary M. Chinigo, Thomas Knauber, David W. C. MacMillan
Summary: In this study, a new synthetic method was reported to form sulfonamides, important amide bioisosteres, by coupling carboxylic acids and amines. This method utilizes copper ligand-to-metal charge transfer (LMCT) to convert aromatic acids to sulfonyl chlorides, followed by one-pot amination to form the corresponding sulfonamide. The method can be applied to a diverse set of substrates and also enables the synthesis of (hetero)aryl sulfonyl fluorides, which have utility in chemical probes and programmable bifunctional reagents.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Applied
Tien Tan Bui, Van Hieu Tran, Hee-Kwon Kim
Summary: This study presents a visible-light-mediated synthesis of sulfonyl fluorides from arylazo sulfones using K2S2O5 and NFSI as reagents, achieving high yields of the products at room temperature. This protocol provides a useful synthetic approach to sulfonyl fluoride structures.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Honghai Zhang, Shaojie Li, Han-Liang Zheng, Gangguo Zhu, Saihu Liao, Xingliang Nie
Summary: Sulfonyl fluorides, known for their unique reactivity and stability, have gained increasing attention from medicinal chemists and chemical biologists. Researchers have developed a novel method for photocatalytic induced synthesis of alkylsulfonyl fluorides based on the SO2 radical insertion/fluorination strategy, enabling the late-stage fluorosulfonylation of natural products and drugs with primary, secondary, and tertiary aliphatic carboxylic acid NHPI esters.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Lei Liu, Long-Yu Ran, Yucheng Gu, Cheng-Pan Zhang
Summary: Tetramethylammonium trifluoromethylselenate has been confirmed as an excellent precursor for selenofluorophosgene, allowing for the preparation of selenocarbamoyl fluorides, selenoureas, and heterocycles without the need for catalysts or additives. The reactions with different types of amines result in the formation of a variety of selenium-containing compounds.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Zhiling Xiang, Congyan Liu, Chunhui Chen, Xin Xiao, Thien S. Nguyen, Cafer T. Yavuz, Qiang Xu, Bo Liu
Summary: Reversible CO2 capture and release under practical conditions is achieved using a single-crystalline guanidinium sulfate-based clathrate salt. The salt has high CO2 density and capacity, and the captured CO2 can be released through moderate means of pressure or temperature stimulation, while the salt is ready for another cycle. The clathrate is selective to CO2 due to specific electrostatic interaction with guanidinium cations, providing a promising avenue for future carbon capture and storage technologies.
CELL REPORTS PHYSICAL SCIENCE
(2023)
Article
Chemistry, Organic
Sunil K. Ghosh
Summary: This article discusses the important role of silicon groups in organic reactions and the unique properties of beta-silylmethylene malonate (beta-SMM) in organic synthesis.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Tao Zhong, Zhida Chen, Jitao Yi, Gui Lu, Jiang Weng
Summary: The SuFEx reaction introduced in 2014 is an efficient and reliable click chemistry tool for creating modular intermolecular connections, attracting significant attention in various fields. This review focuses on the synthetic methods of sulfonyl fluorides to stimulate the development of more efficient methods in this area.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Applied
Xin Qiu, Wenrun Lou, Shengxue Zhang, Shengyajun Meng, Yong Guo, Xiaoyu Ma, Chao Liu, Qilong Shen
Summary: A convenient method for the preparation of the efficient radical difluoromethylthiolation reagent PhSO2SCF2H was reported. The reagent was synthesized on a scale of approximately 500 g from cheap commodity sodium benzene sulfinate, benzyl mercaptan, and HCF2Cl in two steps. The key step of this method involves controlling the amount of chlorine and reaction temperatures to generate the key intermediate [HCF2SCl]. The stability of PhSO2SCF2H was confirmed by differential scanning calorimetry (DSC). Additionally, gram-scale reactions of PhSO2SCF2H with electron-rich aromatic (hetero)-hydrocarbons, alkyl carboxylic acids, and olefins were demonstrated.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2023)
Article
Chemistry, Multidisciplinary
Andrew J. Greener, Patrycja Ubysz, Will Owens-Ward, George Smith, Ivan Ocana, Adrian C. Whitwood, Victor Chechik, Michael J. James
Summary: This study describes the design and development of an oxime-based hydroxylation reagent that can selectively convert aryl halides into phenols under simple, transition-metal-free conditions. The key to success lies in identifying a reducing oxime anion that can interact and couple with open-shell aryl radicals. Experimental and computational studies support the proposed radical-nucleophilic substitution chain mechanism.
Article
Chemistry, Multidisciplinary
Pui Kin Tony Lo, Michael C. Willis
Summary: This study presents a new redox-neutral Ni(II)-catalyzed reaction system for the addition of (hetero)aryl boroxines to N-sulfinyltritylamine to produce sulfinamide products. The initially formed sulfinamides can be further transformed into various compounds through chlorination and hydrolysis. These transformations can all be conducted through one-pot procedures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
