Article
Chemistry, Applied
Sloan Ayers, Gregory L. Beutner, Wei Ding, Carolyn Higman, Charles Pathirana, Robert Wethman
Summary: Having reliable methods to monitor catalyst activation processes is crucial for ensuring the reproducibility of catalytic reactions. For asymmetric Diels-Alder reactions, chiral oxazaborolidine or oxazaborolidinium catalysts are powerful reagents that promote these reactions with high yield and selectivity. By investigating the mechanism, several modern analytical methods are compared to quantitate the formation of oxazaborolidine catalyst from amino alcohol and boroxine, leading to useful monitoring methods for this important transformation.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Polymer Science
Nana Kikuta, Takahiro Shindo, Yu-ki Sugiyama, Takeshi Yamada, Sentaro Okamoto
Summary: The novel synthetic method for hyperbranched polymers utilizes a cobalt catalyst to promote the successful polymerization of aromatic diynes with internal alkynes, resulting in soluble polymers without the production of insoluble materials. The resulting polymer's molecular weight and degree of branching can be controlled by selecting the internal alkyne monomer and adjusting its loading amount.
Article
Chemistry, Physical
Daniele Loco, Isabelle Chataigner, Jean-Philip Piquemal, Riccardo Spezia
Summary: Modeling chemical reactions using Quantum Chemistry is a widely used predictive strategy that complements experimental studies to understand reaction mechanisms. This research benchmarked various computational approaches for predicting energy barriers in six Diels-Alder reactions of increasing complexity. The results showed that using economical Density Functional Theory methods combined with empirical dispersion corrections can provide high-quality results with minimal computational effort. This simulation protocol opens new prospects for studying Diels-Alder reactions with explicit solvent using hybrid QM/MM molecular dynamics simulations.
Article
Chemistry, Organic
Jian-Xiang Zhu, Fu Pi, Teng Sun, Wen-Yu Huang, Lu Gao, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: This article introduces a palladium-catalyzed tandem reaction that proceeds through sequential 2,4-dienylation/Michael addition/pi-sigma-pi isomerization/allylic alkylation. Using ortho-functionalized aryl enones and 2,4-dienyl carbonates as substrates, enantioenriched architectures with fused and spirocyclic frameworks are constructed in moderate to excellent yields and stereoselectivity. Importantly, the intrinsic intramolecular Diels-Alder reaction pattern of the dienylated intermediates is effectively reversed via Pd(0)-pi-Lewis base catalysis.
Article
Chemistry, Multidisciplinary
Guang-Chao Feng, Jun-Chi Li, Xiang Huang, Ji-Kai Liu, Bin Wu, Jin-Ming Yang
Summary: A novel cascade gold(I)-catalyzed hydroarylation of alkynylindoles and subsequent Diels-Alder cycloaddition with electron-deficient alkynes and alkenes is reported herein. The method features low catalyst loadings, high regioselectivity, broad functional group tolerances, access to important heterocycles, and 100% atom economy.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Hongling Wang, Qiangqiang Zhang, Shuai Xiao, Guanjie Wang, Xuan Huang, Xingkuan Chen, Junmin Zhang
Summary: We have developed a N-heterocyclic carbene (NHC) and base-mediated [3 + 3] annulation reaction for the synthesis of enantioselective dihydropyrano[3,2-b]indoles. Easily prepared sulfonium salts were used as precursors and reacted with unsaturated acyl azolium to achieve this transformation. The reaction conditions are mild and result in privileged indole-fused dihydropyranones with moderate to good yields and excellent enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Materials Science, Multidisciplinary
Chirag R. Ratwani, Ali Reza Kamali, Amr M. Abdelkader
Summary: This review summarizes the recent advances in self-healing polymers based on reversible cycloaddition reactions, with a focus on the Diels-Alder (DA) reaction. The principles of the DA reaction and its application in polymers are introduced. The thermodynamics governing the rupture-repair process in self-healing polymers and the use of advanced spectroscopic techniques are discussed, along with their applicability in thermosets, epoxy resins, biopolymers, and polymer nanocomposites.
PROGRESS IN MATERIALS SCIENCE
(2023)
Article
Chemistry, Organic
Lukas Hoff, Simon D. Schnell, Andrea Tomio, Anthony Linden, Karl Gademann
Summary: A silver-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids was presented in this study. It was found that electronic modification of the dppf ligand played a crucial role in achieving good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were successfully prepared, with yields up to 87%.
Article
Chemistry, Multidisciplinary
Huy Tran, Guillaume Revol, Alyson Poyser, Louis Barriault
Summary: In this study, a novel Lewis acid gold catalyst was used to generate synthetically challenging polycyclic scaffolds through a one-pot cascade sequence. By controlling the ligand and reaction conditions, both 6,6,5-tricyclic and 6,6,6,5-tetracyclic cores were selectively synthesized in one operation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Kyu-Hyun Sim, Thameem ul Ansari, Yong-Gyu Park, Yeolib Jeong, Sang-Ha Oh, Hye-Won Min, Da-Yoon Jeon, Hyunwoo Kim, Cheon-Gyu Cho
Summary: This study reports the intramolecular Diels-Alder reactions of 2-pyrones with a chiral branched allylic silyl ether substituent, showing remarkably high pi-facial- and endo-selectivities. The resulting diastereomerically and enantiomerically pure cycloadducts were transformed into the natural products (+)-lycopladine A and (-)-lycoposerramine R.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Hanling Bao, Yabei Wu, Yuhang Jiang, Hao Zhang, Zhiyong Wang
Summary: This study investigates the effects of reduction and oxidation on the reactivity and regioselectivity of metallofullerene La@C-82 in Diels-Alder reaction. It is found that oxidation enhances the reactivity and changes the regioselectivity of the reaction. Energy decomposition analysis reveals that kinetic reactivity of the metallofullerene is determined by exchange-repulsion interaction energy.
CHEMISTRY-AN ASIAN JOURNAL
(2021)
Article
Chemistry, Organic
Julia O. Strelnikova, Alexander N. Koronatov, Nikolai Rostovskii, Alexander F. Khlebnikov, Olesya Khoroshilova, Mariya A. Kryukova, Mikhail S. Novikov
Summary: The domino reaction catalyzed by Rh-2(Piv)(4) leads to the formation of N-sulfonylated (Z)-2-(2-aminovinyl)imidazoles, providing a direct and flexible access to the desired compounds.
Article
Chemistry, Multidisciplinary
Razvan C. Cioc, Marc Crockatt, Jan C. van Der Waal, Pieter C. A. Bruijnincx
Summary: A hydrazine-mediated approach was used to produce renewable aromatics by Diels-Alder aromatization of biobased furfurals. The synthesis of aromatics using this method was selective, simple, and mild.
Article
Chemistry, Organic
Ruyu Xie, Zhiqiang Zhao, Yongxing Zhao, Rui Li, Jinzhong Yao, Maozhong Miao
Summary: Via Cu(I)-catalyzed cycloisomerization, readily available allenyl ketones bearing a cyclopropyl moiety can form in situ furan-fused cyclobutenes, which are highly reactive and powerful species that can undergo annulative fragmentation with terminal ynones to produce a wide variety of functional furans in moderate to high yields. This ring-distortion protocol features an unprecedented strain-controlled cycloisomerization/Diels-Alder/retro-Diels-Alder (CDRD) sequence under mild conditions.
Review
Chemistry, Multidisciplinary
Gangam Srikanth Kumar, Qing Lin
Summary: The merger of click chemistry with discrete photochemical processes has given rise to a new class of reactions known as photoclick chemistry, allowing for rapid and precise synthesis of organic structures under mild conditions. Photoclick chemistry provides unparalleled control over reactive intermediate generation, making it indispensable in spatially addressable applications such as biomolecular labeling and polymer conjugation. Particularly popular are photoclick reactions based on 1,3-dipolar cycloadditions and Diels-Alder reactions due to their excellent reaction kinetics, selectivity, and biocompatibility.
Article
Chemistry, Organic
Philip Jungk, Fabian Fischer, Indre Thiel, Marko Hapke
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Materials Science, Multidisciplinary
Colin Georgi, Marko Hapke, Indre Thiel, Alexander Hildebrandt, Thomas Waechtler, Stefan E. Schulz, Heinrich Lang
Article
Chemistry, Organic
Fabian Fischer, Alexander F. Siegle, Marek Checinski, Christine Fischer, Karolin Kral, Richard Thede, Oliver Trapp, Marko Hapke
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Phillip Jungk, Tobias Taeufer, Indre Thiel, Marko Hapke
SYNTHESIS-STUTTGART
(2016)
Article
Chemistry, Organic
Marko Hapke
TETRAHEDRON LETTERS
(2016)
Article
Chemistry, Physical
Phillip Jungk, Fabian Fischer, Marko Hapke
Article
Chemistry, Multidisciplinary
Volkmar Trommer, Fabian Fischer, Marko Hapke
MONATSHEFTE FUR CHEMIE
(2018)
Article
Chemistry, Organic
Fabian Fischer, Marko Hapke
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Physical
Indre Thiel, Marko Hapke
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
(2014)
Article
Chemistry, Inorganic & Nuclear
Barbara Heller, Marko Hapke, Christine Fischer, Angelina Andronova, Ivo Stary, Irena G. Stara
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2013)
Article
Chemistry, Inorganic & Nuclear
Indre Thiel, Haijun Jiao, Anke Spannenberg, Marko Hapke
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2014)
Article
Chemistry, Organic
Paul Stehrer, Anke Spannenberg, Marko Hapke
Summary: This study reports a method for the atroposelective iridium-catalyzed borylation of menthyloxy-substituted phthalazine heterobiaryls, and demonstrates further functionalization of the borylated product with stereoretention.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Benedikt N. Baumann, Helge Lange, Felix Seeberger, Philipp Bueschelberger, Robert Wolf, Marko Hapke
Summary: In this study, highly reduced anthracene and naphthalene cobaltates and ferrates were found to catalyze the cyclization of diynes and triynes, resulting in the expected cycloaddition products as well as unexpected annulation products. Additionally, the solvent was found to significantly affect the substrate conversion rate.
MOLECULAR CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Indre Thiel, Moritz Horstmann, Phillip Jungk, Sonja Keller, Fabian Fischer, Hans-Joachim Drexler, Detlef Heller, Marko Hapke
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Multidisciplinary
Davide Brenna, Matteo Villa, Tim N. Gieshoff, Fabian Fischer, Marko Hapke, Axel Jacobi von Wangelin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Inorganic & Nuclear
Guojun Hu, Ziyue Deng, Yanwei Wang, Dan Yuan, Yong Zhang, Yingming Yao
Summary: A series of rare-earth metal complexes were synthesized and used as efficient initiators for the polymerization of trimethylene carbonate (TMC) and (L)-lactide ((L)-LA).
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Van Ha Nguyen, John H. K. Yip
Summary: In this study, eight PtII-azulene complexes were synthesized to investigate the effect of metalation on the electronic structures, spectroscopy, and luminescence of organic chromophores. The results showed that the attachment of Pt substituents to azulene affected the HOMOs, LUMOs, and luminescence properties. The study provides insights into the role of metalation in modifying the properties of organic chromophores.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Moon Kedia, Virender Singh, Bhaskaran Shankar, Malaichamy Sathiyendiran
Summary: This study synthesized two types of neutral binuclear metallocycles using a one-pot solvothermal method and characterized their structures. The analysis revealed that these complexes adopt a binuclear heteroleptic cyclic architecture and belong to phosphine oxide donor (P=O)-based supramolecular coordination cyclic complexes.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Radhey S. Srivastava
Summary: This study demonstrates the effectiveness of zero-valent elements as reductants for the deoxydehydration reaction of polyols catalyzed by ONO-pincer ligated molybdenum dioxo. The insolubility and easy separability of the reductants and their oxidized products during the reaction are emphasized. Additionally, the choice of ligand has an impact on the catalytic performance of the reaction.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Hao Zhou, Yajun Sun, Li Deng, Weiran Yang, Yuehui Li
Summary: Efficient Ru-catalyzed hydrogenation of aldehydes was achieved using carbazole-derived phosphine ligands, with the crucial role of N-H moiety in promoting the catalytic reaction. The method was successfully applied in the Co/Ru-catalyzed hydroformylation process, resulting in the production of long-chain alcohols with excellent yields.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Theodor Danescu, Alexandru Lupan, Radu Silaghi-Dumitrescu, R. Bruce King
Summary: The structures and energies of complexes containing (Me2C2N2P)2Ru2(CO)n and (Me2C2N2P)2Fe2(CO)n have been studied. Low-energy structures are characterized by the presence of bridging diazaphospholyl rings, while higher-energy structures involve different ligand structures.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Savannah C. Kapper, Aamani Ponnekanti, Jonas Schaab, Tian-yi Li, Christine L. Chung, Gael Ung, Peter I. Djurovich, Mark E. Thompson
Summary: Organometallic iridium complexes with two cyclometalated ligands and one bis-oxazoline derived ancillary ligand were studied. These complexes have emission spanning across the visible and near-ultraviolet region, with moderate to high photoluminescence quantum yields. The (ppy)2Ir(BOX-CN) complexes were resolved into Delta- and Lambda-diastereomers based on solubility differences.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Zahra Karimi Sangari, Hossein Naeimi
Summary: In this research, a nanostructured CoCuFe2O4 catalyst was prepared using a brief and useful synthetic strategy. This catalyst was used for synthesizing 1,2,4,5-tetrasubstituted imidazole derivatives under ultrasonic irradiation. The approach offers advantages such as high efficiency, short reaction times, simplicity of the reaction medium, accelerated reaction rates, and easier separation and purification of products.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Rukhsana Gul, Wajid Munir, Ebraheem Abdu Musad Saleh, Shaukat Shujah, Muhammad Sirajuddin, Saira Tabassum, Khalil Ur Rehman, Dilfaraz Khan, Sameerah I. Al-Saeedi, Ehab A. Abdelrahman
Summary: Two new Schiff base ligands were synthesized and used to form copper, nickel, and cobalt complexes. The synthesized compounds were characterized and screened for various biological activities. The metal complexes showed better activities in antibacterial, antifungal, antidiabetic, and antioxidant assays.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Review
Chemistry, Inorganic & Nuclear
Ahsan Nazir, Pengwei Huo, Ameena Tur Rasool
Summary: This review explores the potential of g-C3N4-based S-scheme heterojunctions in addressing environmental issues. It summarizes the mechanism and preparation techniques of S-scheme heterojunctions based on g-C3N4, and presents recent studies on their applications in pollutant removal, CO2 reduction, hydrogen production, and bacterial disinfection. The review concludes with an outlook on future challenges for g-C3N4-based S-scheme heterojunctions.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Francois Mazars, Koffi Senam Etse, Guillermo Zaragoza, Lionel Delaude
Summary: The activity of three Pd-PEPPSI catalyst precursors with N-heterocyclic carbene (NHC) ligands derived from caffeine and theophylline in Mizoroki-Heck reactions was tested. The results showed that the catalysts achieved high conversions and yields, especially in the presence of electron-withdrawing substituents.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Bo-Han Wu, Xue Zhou, Lin Liu, Zheng-Bo Han
Summary: Researching carbon dioxide removal from flue gas and natural gas is crucial. Metal-organic frameworks (MOFs) are commonly used in adsorption due to their high surface area, porosity, and chemical properties. An ultra-microporous MOF CPM-20(Co) with mixed ligand was synthesized using inexpensive ligands. The material exhibited high selectivities and low regenerative energy, making it a promising option for CO2 separation in industries.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)