Article
Chemistry, Organic
Aleksandra Nilova, Bryan Metze, David R. Stuart
Summary: Controlling reaction pathways selectively leads to a broad scope of arenes and arynophiles, offering efficient access to diverse arene chemical space and biologically active compounds with high yields.
Article
Chemistry, Multidisciplinary
Shubhendu S. Karandikar, Avik Bhattacharjee, Bryan E. Metze, Nicole Javaly, Edward J. Valente, Theresa M. McCormick, David R. Stuart
Summary: Diarylhalonium compounds play important roles as reagents and catalysts in organic synthesis, with the key reactivity of the three center, four electron bond requiring refinement for broader applicability. The combination of Density Functional Theory, Natural Bond Orbital Theory, and X-ray structure data can provide insights into the bonding and structure of these compounds.
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, Multidisciplinary
Romain Sallio, Pierre-Adrien Payard, Pawel Pakulski, Iryna Diachenko, Indira Fabre, Sabine Berteina-Raboin, Cyril Colas, Ilaria Ciofini, Laurence Grimaud, Isabelle Gillaizeau
Summary: This work presents a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts, leading to N-arylacetamides. The method is characterized by high efficiency, broad substrate scope, and excellent functional group tolerance.
Article
Chemistry, Multidisciplinary
Aleksandra Nilova, Paul A. Sibbald, Edward J. Valente, Gisela A. Gonzalez-Montiel, H. Camille Richardson, Kevin S. Brown, Paul Ha-Yeon Cheong, David R. Stuart
Summary: This study describes a method for synthesizing 1,2,3,4-tetrasubstituted benzenoid rings, addressing previous challenges in regioselective synthesis of these compounds. By using substituted arynes derived from aryl(Mes)iodonium salts, a range of densely functionalized 1,2,3,4-tetrasubstituted benzenoid rings can be accessed. The study demonstrates improved conditions for generating arynes at room temperature and in shorter reaction times, allowing for post-synthetic elaboration via palladium-catalyzed coupling.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Hend Besrour, Matthieu Hedouin, Lina Truong, Sami Lakhdar, Hassan Oulyadi
Summary: In this study, the interaction between a diphenyliodonium salt and trivalent phosphorus compounds was investigated using {H-1, F-19, P-31} NMR and DFT calculations. The importance of blue light in the reaction was highlighted, and the formation of a phosphonium intermediate was identified. The formation of an EDA complex was characterized, and the significance of acetonitrile for the formation of this complex was demonstrated. The study was further extended to other phosphonium salt formation reactions, and the stability and photoreactivity of the complexes were investigated using DFT calculations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Alexandra Pacheco-Benichou, Eugenie Ivendengani, Ioannis K. Kostakis, Thierry Besson, Corinne Fruit
Summary: The copper-catalyzed Csp2-Csp2 bond forming reactions through C-H activation offer a useful strategy for the diversification of heterocyclic moieties. Specific phenylation of fused-pyrimidinones, including quinazolinone, has been achieved using this method, leading to the rapid access of various arylated N-containing polyheteroaromatics as potential bioactive compounds.
Review
Chemistry, Multidisciplinary
Cheng Pan, Limin Wang, Jianwei Han
Summary: This account summarizes our research interest in synthetic methodology with diaryliodonium salts. In addition to employing a dual activation strategy of C-I and ortho C-H bonds, we have introduced vicinal functional groups at the ortho-positions of diaryliodonium salts and explored their unique reactivities in various processes, including arylation, diarylation, cascade annulation, benzocyclization, arylocyclization, and intramolecular aryl migration. The diverse mechanisms of these reactions involving transition metals, especially palladium in organometallic catalysis, or transition-metal free conditions, are discussed in the context.
Article
Chemistry, Organic
Maxime Bouquin, Florian Jaroschik, Marc Taillefer
Summary: A ligand and base-free copper catalyzed synthetic method for the efficient alpha-arylation of aromatic ketones is described in this study. Ketone-derived silyl enol ethers were used to avoid strong bases in the reaction, providing intermolecular C-C coupling with good functional group tolerance and requiring low catalyst loading.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Yohann Landrain, Gwilherm Evano
Summary: An efficient copper-catalyzed inter/intramolecular oxy/aminoarylation of gamma-hydroxy/aminoalkenes with diaryliodonium triflates is described. Activation of the arylating agents and the alkene with copper(II) triflate in dichloromethane leads to the formation of highly substituted tetrahydrofurans and pyrrolidines, depending on the nature of the internal nucleophile. The cyclization process is stereospecific and can also be extended to oxyalkynylation.
Review
Chemistry, Medicinal
Thierry Besson, Corinne Fruit
Summary: This review highlights recent synthetic advances in the late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagents, and discusses their applications in the synthesis of new arylated bioactive heterocyclic compounds.
Article
Chemistry, Organic
Aaron J. Day, Timothy C. Jenkins, Marvin Kischkewitz, Kirsten E. Christensen, Darren L. Poole, Timothy J. Donohoe
Summary: A method for C-4 alkylation of isoquinolines using benzoic acid as a nucleophilic reagent and vinyl ketones as an electrophile is described in this study. The reaction demonstrates tolerance towards substitutions at C-3 and C-5-C-8 positions while allowing variation of vinyl ketone electrophiles. The resulting products contain a carbonyl functional group, which can be used as a synthetic handle for further transformations to obtain esters, amines, or simple alkyl products.
Review
Chemistry, Organic
Dan Wang, Qian Li, Mengting Li, Zhengyin Du, Ying Fu
Summary: Hypervalent iodine compounds, in particular diaryliodonium salts, have been widely used in organic synthesis due to their low toxicity, mild conditions, and high selectivity. These compounds serve as efficient alternatives to heavy metal-based oxidants and expensive organometallic catalysts, showing good reactivity and selectivity in various transformations.
CURRENT ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Avery J. To, Graham K. Murphy
Summary: In this study, it was discovered that cyclic diaryliodonium salts can act as effective Lewis-acidic halogen-bond donor catalysts in the Nazarov cyclization reaction.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhiyuan Bao, Chao Chen
Summary: An efficient method for the synthesis of multi-substituted cyclic imides was developed using cyanoesters and diaryliodonium salts. This method involves a cascade of N-arylation-acylation and rearrangement reactions, producing the desired heterocycles in high yields. The method has a broad substrate scope, excellent functional group compatibility, and can be extended to fused cyclic imides.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Marc Montesinos-Magraner, Matteo Costantini, Rodrigo Ramirez-Contreras, Michael E. Muratore, Magnus J. Johansson, Abraham Mendoza
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Organic
Danny K. H. Ho, Jonas Calleja, Matthew J. Gaunt
Review
Chemistry, Multidisciplinary
Chuan He, William G. Whitehurst, Matthew J. Gaunt
Article
Chemistry, Multidisciplinary
William G. Whitehurst, J. Henry Blackwell, Gary N. Hermann, Matthew J. Gaunt
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Applied
Elisa Martinez-Castro, Samuel Suarez-Pantiga, Abraham Mendoza
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2020)
Article
Chemistry, Multidisciplinary
Ferran Planas, Stefanie V. Kohlhepp, Genping Huang, Abraham Mendoza, Fahmi Himo
Summary: The dynamic equilibria of organomagnesium reagents are studied using DFT calculations and kinetic experiments to investigate the Pummerer coupling between sulfoxides and turbo-organomagnesium amides. Heterometallic open cubane structures are shown to play a key role as reactive intermediates in turbo-organomagnesium amide mixtures through a concerted anion-anion coupling/S-O cleavage step. This research introduces a new reaction pathway and sheds light on the importance of open cubane organometallics in these mixtures.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Ferran Planas, Matteo Costantini, Marc Montesinos-Magraner, Fahmi Himo, Abraham Mendoza
Summary: The study found that the slower dimerization reaction of NHPI-DA catalysis led to better selectivity; calculations showed multiple reaction pathways for the cyclopropanation of NHPI-DA, with carbene insertion being a key step; the stereoselectivity of the reaction depends on the intricate balance between various mechanistic scenarios.
Editorial Material
Chemistry, Multidisciplinary
Kilian Colas, A. Catarina V. D. dos Santos, Stefanie Kohlhepp, Abraham Mendoza
Summary: In this study, the researchers enhanced the nucleophilicity and selectivity of Grignard reagents by introducing a bulky magnesium anilide additive, resulting in the direct synthesis of ketones from carboxylic acids.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Kilian Colas, A. Catarina V. D. dos Santos, Stefanie Kohlhepp, Abraham Mendoza
Summary: The addition of organometallic reagents to aliphatic carboxylic acids for the synthesis of ketones is limited to organolithium reagents, but can be extended to Grignard reagents using a bulky aniline-derived turbo-Hauser base. This method allows for the straightforward preparation of a variety of aliphatic and perfluoroalkyl ketones.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Matteo Costantini, Abraham Mendoza
Summary: A modular approach from olefin materials to the synthesis of chiral cis-cyclopropanes is enabled by the discovery of the electron donor-acceptor interaction between 2-substituted benzothiazolines and N-hydroxyphthalimide esters. These complexes are activated by visible light without photocatalysts, with benzothiazoline reagent serving as a photoreductant, stereoselective hydrogen-atom donor, and a Bronsted acid. This study introduces benzothiazolines as accessible and easily tunable self-sensitized photoreductants, expanding their potential applications beyond enantioselective synthesis of cis-cyclopropanes.
Article
Chemistry, Organic
Rajdip Chowdhury, Gabor Zoltan Elek, Beatriz Meana-Baamonde, Abraham Mendoza
Summary: (Borylmethyl)trimethylsilanes are important building blocks with unique reactivity in organic synthesis. However, the synthesis of more advanced derivatives is limited due to the requirement of advanced silicon intermediates. This study develops a one-pot synthesis of (borylmethyl)silanes using available alkyl, aryl, alkoxy, aryloxy, and silyl-hydrosilane materials. The reactivity of N-hydroxyphthalimidyl diazoacetate (NHPI-DA) in Si-H insertion and alpha-silyl redox-active esters in different decarboxylative borylation reactions is investigated.
Article
Chemistry, Multidisciplinary
Rajdip Chowdhury, Abraham Mendoza
Summary: This study investigates the use of redox-active carbenes in the expedited and divergent synthesis of functionalized indoles, showing high efficiency and selectivity with NHPI-DA. The method allows for swift elaboration of insertion products into boron and carbon substituents.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Rajdip Chowdhury, Zhunzhun Yu, My Linh Tong, Stefanie Kohlhepp, Xiang Yin, Abraham Mendoza
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Emma Bratt, Samuel Suarez-Pantiga, Magnus J. Johansson, Abraham Mendoza
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Cornelia S. Buettner, Darren Willcox, Ben. G. N. Chappell, Matthew J. Gaunt
Article
Chemistry, Multidisciplinary
Alexander M. Prophet, Kritanjan Polley, Gary J. Van Berkel, David T. Limmer, Kevin R. Wilson
Summary: The oxidation kinetics of iodide by ozone at the air-water interface is studied in single microdroplets. Molecular simulations and kinetic modeling are used to understand the underlying multiphase mechanism.
Article
Chemistry, Multidisciplinary
Rong Zhang, Jiajing Lan, Fei Wang, Shumei Chen, Jian Zhang
Summary: By utilizing 1,1'-ferrocene dicarboxylic acid as a chelating and surface protection ligand, we have synthesized multi-nuclear indium oxide clusters with varying nuclear sizes, including heptanuclear and thirteen-nuclear clusters. These clusters possess labile coordination sites, allowing for structural modification and self-assembly, resulting in the formation of various cluster structures.
Article
Chemistry, Multidisciplinary
Hui Wang, Hui Liu, Mingsen Wang, Jiaheng Hou, Yongjun Li, Yuancheng Wang, Yingjie Zhao
Summary: Two supramolecular complexes were prepared using CBs and M1, and their single-crystal structures were analyzed by SCXRD. The unexpected 1:2 self-assembly structure between M1 and CB[8] was discovered for the first time. These complexes exhibit unique photophysical properties and provide valuable information about the structure and photophysical properties of supramolecular complexes.
Article
Chemistry, Multidisciplinary
Chang-Hee Lee, Sookil Park, Sanggil Kim, Ji Young Hyun, Hyun Soo Lee, Injae Shin
Summary: The epidermal growth factor receptor (EGFR) is a cell-surface glycoprotein involved in cell proliferation and tumor development. This study used a fluorescently labeled EGFR to investigate its time-dependent endocytosis in live cells and found that appended glycans affect EGFR internalization. Additionally, the study detected sialic acid residues attached to EGFR on the live cell surface using FRET-based imaging. This research provides valuable insights into the cellular functions of EGFR.
Article
Chemistry, Multidisciplinary
Subhankar Sahu, Lokesh Kumar, Sumita Das, Dipti Gupta, Ruchi Anand
Summary: This study proposes a strategy that combines organic electronics with biosensor scaffolds to create a compact device for monitoring environmental aromatic pollution. By coupling biosensing protein MopR with an organic electrochemical transistor (OECT), a sensor module capable of efficient detection of phenol was designed. Exclusive phenol detection with minimal loss of sensitivity could be achieved in complex pollutant mixtures and real environmental samples.
Review
Chemistry, Multidisciplinary
Changseok Lee, Hyung-Joon Kang, Sungwoo Hong
Summary: The formation of C-N bonds through hydroamination reactions catalyzed by nickel hydrides has been a topic of recent interest. This approach offers a way to efficiently transform a variety of alkene and alkyne substrates into compounds enriched with C-N bonds. The review provides a concise overview of the underlying reaction mechanisms and aims to stimulate further progress in NiH-catalytic techniques and catalyst design.
Article
Chemistry, Multidisciplinary
Yueci Wu, Lu-Lu Sun, Hai-Hao Han, Xiao-Peng He, Weiguo Cao, Tony D. James
Summary: Drug-induced liver injury (DILI) is a common cause of acute liver failure in the USA and Europe, but most cases can be recovered or prevented by discontinuing the offending drug. Recent research has found that peroxynitrite (ONOO-) can be used as a potential indicator for early diagnosis of DILI, and there is an urgent need to establish a method to detect and track peroxynitrite in DILI cases. In this study, a FRET-based nano fluorescent probe CD-N-I was developed, which showed high selectivity and sensitivity in detecting peroxynitrite. The probe successfully detected exogenous peroxynitrite in live cells and endogenous peroxynitrite in APAP-induced liver injury of HepG2 cells.
Article
Chemistry, Multidisciplinary
Dmitry L. Lipilin, Mikhail O. Zubkov, Mikhail D. Kosobokov, Alexander D. Dilman
Summary: This article describes a direct photocatalytic method for the thiolation of unprotected acids, which was previously challenging. By using a thionocarbonate reagent with an N-O bond, the efficient conversion of carboxylic acids to thiols is achieved.
Article
Chemistry, Multidisciplinary
Jason Malenfant, Lucille Kuster, Yohann Gagne, Kouassi Signo, Maxime Denis, Sylvain Canesi, Mathieu Frenette
Summary: Raman microscopy can reveal compound-specific vibrational fingerprints without sample preparation. The combination of efficient theoretical calculations and a user-friendly software can accurately predict peak positions and provide match scores to assist with structure determination.
Article
Chemistry, Multidisciplinary
Jayoh A. Hernandez, Paul S. Micus, Sean Alec Lois Sunga, Luca Mazzei, Stefano Ciurli, Gabriele Meloni
Summary: Essential trace metals play crucial roles in the survival and virulence of bacterial pathogens. Helicobacter pylori requires nickel for colonization and persistence in the stomach, and NixA is an essential nickel transporter in this process. This study characterizes the selectivity and electrogenic nature of NixA-mediated nickel transport.
Article
Chemistry, Multidisciplinary
Tarali Devi, Kuheli Dutta, Jennifer Deutscher, Stefan Mebs, Uwe Kuhlmann, Michael Haumann, Beatrice Cula, Holger Dau, Peter Hildebrandt, Kallol Ray
Summary: This study emphasizes the importance of subtle electronic changes and secondary interactions in the stability of biologically relevant metal-dioxygen intermediates. It also shows that the role of the chloride ligand in stabilizing the Fe-III-(OOBu)-Bu-t moiety can extend to other anions, including the thiolate ligand.
Article
Chemistry, Multidisciplinary
Jacqueline R. Santhouse, Jeremy M. G. Leung, Lillian T. Chong, W. Seth Horne
Summary: By studying the folding kinetics and mechanism of the BdpA sequence, researchers found that altering the backbone connectivity can affect protein folding. This suggests that protein mimetic chains have a significant degree of plasticity in transitioning between unfolded and folded states.
Article
Chemistry, Multidisciplinary
Divanshu Gupta, Ralf Einholz, Holger F. Bettinger
Summary: This study presents the first direct spectroscopic evidence of a cyclic seven-membered iminoborane. Compared to linear amino-iminoboranes, this cyclic iminoborane exhibits weakened bond strength and lower Lewis acidity value. The study suggests that the reduced ring strain of cyclic iminoborane prevents nitrogen fixation but allows facile (2 + 2) cycloaddition reaction with C2H4.
Article
Chemistry, Multidisciplinary
Renny Mathew, Aniruddha Mazumder, Praveen Kumar, Julie Matula, Sharmarke Mohamed, Petr Brazda, Mahesh Hariharan, Brijith Thomas
Summary: This study reveals the packing arrangement of partially disordered nitro-perylenediimide (NO2-PDI) using a synergistic approach that combines 3D ED, ssNMR, and DFT techniques. By overcoming these challenges, this methodology opens up new avenues for material characterization, driving exciting advancements in the field.
