Review
Chemistry, Multidisciplinary
Myuto Kashihara, Yoshiaki Nakao
Summary: Cross-coupling reactions using nitroarenes as electrophiles have gained attention due to their ease of accessibility and potential advantages over haloarenes. Recent research has focused on developing new catalyst systems and reaction conditions to improve the efficiency and practicality of these reactions, with promising results in diversifying bond-forming reactions and reducing catalyst loading. Research in this field is expected to continue growing as the utility of nitroarenes in organic synthesis is reevaluated.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Nanoscience & Nanotechnology
Eadaoin Casey, Justin D. Holmes, Gillian Collins
Summary: This study reports a one-pot synthesis of surfactant templated PdAu nanosheets and investigates their catalytic performance in light-enhanced Suzuki cross coupling reactions. The PdAu bimetallic nanosheets demonstrate higher catalytic activity compared to monometallic Pd nanosheets and commercial Pd/C at room temperature.
ACS APPLIED NANO MATERIALS
(2022)
Review
Chemistry, Multidisciplinary
Emily K. Reeves, Emily D. Entz, Sharon R. Neufeldt
Summary: Chemodivergent cross-couplings refer to reactions in which one potentially reactive functional group can be made to react based on choice of conditions. Factors influencing selectivity include catalyst ligation state, solvent polarity, and metal identity.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Zhenghong Zhou, Jimin Yang, Bo Yang, Yang Han, Lijuan Zhu, Xiao-Song Xue, Feng Zhu
Summary: This study presents a pioneering example of nickel-catalysed enantioconvergent Stille cross-coupling reactions. The reactions result in the formation of C-C bonds in good to high yields with excellent stereoselectivity, providing a practical and cost-effective method for synthesis. The innovative use of synergistic photoredox/nickel catalysis enables a novel single-electron transmetalation process, opening up new research possibilities in the field of Stille reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Felipe Verdugo, Ricardo Rodino, Martin Calvelo, Jose Luis Mascarenas, Fernando Lopez
Summary: The reactivity of carbonyl-tethered alkylidenecyclopropanes (ACPs) can be directed towards tandem cycloisomerization/cross-coupling processes by using Pd-0 catalysts with phosphorus-based monodentate ligands. This allows for the synthesis of a wide variety of highly functionalized cyclic alcohols and amines through the formation of key pi-allyl oxapalladacyclic intermediates which are trapped with external nucleophilic partners.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Chiara Palladino, Tommaso Fantoni, Lucia Ferrazzano, Beatrice Muzzi, Antonio Ricci, Alessandra Tolomelli, Walter Cabri
Summary: The copper-free Heck-Cassar-Sonogashira (HCS) reaction is a powerful method for C-C bond formation in organic synthesis and has several industrial applications. This study investigated the mechanism of the copper-free HCS reaction by conducting stoichiometric and catalytic reactions and analyzing the role of the base. The results showed that the base can accelerate the reduction of the precatalyst and decrease the energy barrier for the alkyne carbopalladation step.
Article
Chemistry, Multidisciplinary
Jordi Aragon, Suyun Sun, David Pascual, Sebastian Jaworski, Julio Lloret-Fillol
Summary: This study presents a strategy for activating inert alkyl chlorides through photoredox catalysis and using them as coupling partners with alkenes. The catalytic system involves the activation of Csp(3)-Cl bonds by [Ni(OTf)(Py(2)(Ts)tacn)](OTf) (1(Ni)) and photoredox catalysis by [Ir((NMe2)bpy)(ppy)(2)]PF6 (PCIrNMe2). Experimental and theoretical studies show that the catalytic system can cleave Csp(3)-Cl bonds of alkyl chlorides via an S(N)2 mechanism, leading to the formation of carbon-centered free radicals that react with alkenes to form Csp(3)-Csp(3) bonds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Turbasu Sengupta, Dinesh Bista, Shiv N. Khanna
Summary: The doping of a Pd cluster with Ag atoms enhances the efficiency of Suzuki-Miyaura cross-coupling reactions by reducing the barriers for oxidation and reduction steps. The Ag atom adjacent to Pd sites in a Pd12Ag cluster donates charge to lower the barriers, demonstrating a unique donor-acceptor characteristic between Ag and Pd atoms. This study shows that altering the active site atom can control the activation energies of redox steps, suggesting the potential of silver-doped Pd-n clusters as catalysts.
Article
Chemistry, Applied
Ahmed R. Abdellah, Abu-Bakr AAM. El-Adasy, Ahmed A. Atalla, Kamal I. Aly, Hani Nasser Abdelhamid
Summary: In this study, COFs synthesized via the solvothermal method were used as supports for in-situ growth of Pd NCs, resulting in catalysts with small particle sizes. The materials were characterized using various techniques, and the Pd NCs@COFs exhibited excellent catalytic performance and stability in C-C formation reactions.
MICROPOROUS AND MESOPOROUS MATERIALS
(2022)
Article
Chemistry, Organic
Ivan Rodriguez-Oliva, Noelia Losada-Garcia, A. Sofia Santos, M. Manuel B. Marques, Jose M. Palomo
Summary: Highly stable nanocatalysts were synthesized in aqueous medium at room temperature by in situ formation of Pd nanoparticles embedded in an enzyme net. The synthesized CALB/PdNPs hybrids showed crystalline Pd(0) as the unique metallic species, with spherical nanoparticles ranging in diameter size from 2 to 11 nm. These hybrids were employed as catalyst in C-N/Heck reaction cross-coupling cascade to synthesize substituted azaindoles with high selectivity.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Weixu Lu, Xiaoqiang Yu, Ming Bao
Summary: In this paper, a group of copper-based ternary deep eutectic solvents (Cu-DESs) were synthesized and applied in Glaser-type homo- and cross-coupling of terminal alkynes. These reactions occurred under exogenous-ligand-free, base-free, and additive-free conditions, providing satisfactory to excellent yields (up to 99%) under mild conditions. The Cu-DESs can be recycled eight times, with water being the only by-product, complying fully with the principles of green chemistry.
Article
Materials Science, Paper & Wood
Zhian Xu, Jinxi Xu, Waner Zheng, Yiqun Li
Summary: A novel and efficient cellulose-based Pd@Cell-EDTA catalyst was easily prepared through the esterification of cellulose with ethylenediaminetetraacetic dianhydride and subsequent coordination with PdCl2. The Pd@Cell-EDTA catalyst showed excellent activity in Suzuki reactions and Sonogashira reactions, and it could be reused multiple times without significant loss of catalytic performance.
Article
Chemistry, Physical
Victoria Dimakos, Daniel P. Canterbury, Sebastien Monfette, Philipp C. Roosen, Stephen G. Newman
Summary: This study describes a Pd-catalyzed method for the direct and selective alpha-arylation of cyclic enones using (hetero)aryl triflates. Optimized ligands and additives were employed to achieve high selectivity. Preliminary mechanistic investigations suggest that the reaction proceeds through enone activation and Pd-catalyzed enolate arylation, resembling a Morita-Baylis-Hillman reaction.
Article
Chemistry, Physical
Guang-Yan Xing, Ya-Cheng Zhu, Deng-Yuan Li, Pei-Nian Liu
Summary: On-surface synthesis, a powerful tool for atomically precise fabrication of low-dimensional carbon nanomaterials, has greatly enriched fundamental science and technology. Achieving high selectivity of covalent coupling reactions remains challenging due to the complicated reactivity of organic groups and irreversibility of covalent bonds. Only a few on-surface covalent coupling reactions are frequently used, and this Perspective focuses on the development and synthetic applications of on-surface cross-coupling reactions.
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2023)
Review
Chemistry, Physical
Agnes Mastalir, Arpad Molnar
Summary: Noble metal nanoparticles supported on porous silica materials have gained significant research progress in recent years. The focus is on the development of highly dispersed Pd0 nanoparticles immobilized on porous silica materials, which have proven to be efficient and recyclable catalysts in C-C coupling and cross-coupling reactions.
Article
Chemistry, Multidisciplinary
Lipeng He, Hung-Kai Hsu, Lijie Li, Lin-Ting Lin, Tsung-Han Tu, Tiow-Gan Ong, Gunn-Guang Liou, Yi-Tsu Chan
Summary: This study successfully constructs a 10-nm-sized cuboctahedron through dynamic heteroleptic complexation and multivalent ligand design. The cuboctahedron has a double-layered multicompartment structure and can self-assemble into ordered square arrays. Cryogenic electron microscopy reveals dislocations and grain boundaries of packing domains, which result in the formation of oblique arrays. This research provides a foundation for the bottom-up development of uniform two-dimensional materials.
Article
Multidisciplinary Sciences
Keat Ying Chan, Ching-Cher Sanders Yan, Hsiao-Yuh Roan, Shao-Chun Hsu, Tzu-Lun Tseng, Chung-Der Hsiao, Chao-Ping Hsu, Chen-Hui Chen
Summary: This study reveals the mechanism of epithelial coverage expansion during animal development. Skin cells continue to divide even without DNA replication, causing a reduction in genome size. Manipulation of body surface growth affects the division of skin cells. This mode of cell proliferation may occur in contexts other than zebrafish skin expansion.
Article
Multidisciplinary Sciences
Erickson Fajiculay, Chao-Ping Hsu
Summary: In this study, a Python-based software was developed that supports symbolic, deterministic, and stochastic modeling, along with parameter estimation and SBML support. The software is reliable, well performing, and convenient to use, providing better availability and accessibility for studying kinetics and dynamics in biochemical systems.
Article
Materials Science, Multidisciplinary
Fang-Ju Lin, Yao-Jin Ke, Kai-Yuan Kuan, Chao-Ping Hsu, Yu-Tai Tao
Summary: Films of well-aligned linear diacetylenic acid were prepared and photopolymerized using the solution-shearing method. The direction of molecular alignment and polymer chains varied depending on the polarity of the solvent used during the shearing process. Transistors based on these films showed highly anisotropic field-effect mobilities, with the highest mobility obtained from films prepared from a hexane solution.
ACS APPLIED POLYMER MATERIALS
(2022)
Article
Agriculture, Multidisciplinary
Hsin-Ya Tsai, Ming-Yu Chen, Chen Hsu, Kai-Yuan Kuan, Chi-Fon Chang, Che-Wei Wang, Chao-Ping Hsu, Nan-Wei Su
Summary: This study revealed the bioconversion of luteolin by Bacillus subtilis BCRC 80517, resulting in the production of three water-soluble phosphate conjugates. It was found that luteolin disrupted bacterial membrane integrity, leading to incomplete conversion. Additionally, a spontaneous intramolecular transesterification of one of the derivatives was observed under acidic conditions.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hao-Lan Zhang, Yuan-Qi Zhai, Hiroyuki Nojiri, Christian Schroeder, Hung-Kai Hsu, Yi-Tsu Chan, Zhendong Fu, Yan-Zhen Zheng
Summary: This study presents a method for spin wave excitation using heterometallic rings and predicts spin wave excitations at different temperatures. The study finds that antiferromagnetic exchange, dipole-dipole interaction, and ring topology play important roles in spin wave excitations at low temperatures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Erickson Fajiculay, Chao-Ping Hsu
Summary: Noise in biochemical networks is of importance in biological problems, and understanding noise dynamics through network structure analysis is desirable. This study developed a noise localization theory that identifies buffering structures and provides insights into noise flow under non-steady-state conditions.
Article
Materials Science, Multidisciplinary
Thomas Baeatz, Ilya Anufriev, Chiao-Hsuan Pai, Timo Schuett, Ivo Nischang, Stefan Zechel, Martin D. Hager, Yi-Tsu Chan, Ulrich S. Schubert
Summary: Miktoarm star polymers are a type of branched polymers with a star-shaped architecture based on different assembly properties. The synthesis of these polymers can be challenging, especially when using covalent strategies to link different polymers. This study presents an approach using orthogonal metal-ligand interactions to connect the building blocks and create miktoarm topology. The structures obtained are investigated using diffusion-ordered nuclear magnetic resonance spectroscopy, analytical ultracentrifugation, and dynamic light scattering.
ACS APPLIED POLYMER MATERIALS
(2023)
Article
Chemistry, Physical
Chen-Hsun Hung, Ting-Hsuan Wang, Glenn P. A. Yap, Joon Ching Juan, Tiow-Gan Ong
Summary: This study presents a Ni-catalyzed heteroarene C-H/arenol C-OH coupling reaction without the need for strong Lewis-acid additive and low atom-economy protecting reagent. A range of arenols and heteroarenes can be effectively catalyzed using an in-situ activating reagent of pivalic anhydride. Mechanistic studies and identification of intermediates have been conducted to understand the nature of the catalytic reactions.
Article
Chemistry, Multidisciplinary
Erickson Fajiculay, Chao-Ping Hsu
Summary: One of the primary interests in understanding biological systems is to study the interaction between noise and cellular regulation. This study explores steady-state perturbations of monomolecular closed systems and ways to estimate the response of noise as (co)variances. The findings provide potential applications in model discrimination, network-wide response scanning, and reconstruction.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2023)
Article
Chemistry, Inorganic & Nuclear
Bamlaku Semagne Aweke, Cheng-Han Yu, Jiun-Shian Shen, Sheng Wang, Glenn P. A. Yap, Wen-Ching Chen, Tiow-Gan Ong
Summary: In this study, a carbone-transfer agent Ag-I complex of a bis(carbone) pincer ligand was synthesized, which eliminated the requirement for isolating the free ligand. The complex was efficiently used to transfer the ligand to other transition metals. This approach has potential for isolating metal complexes of carbone ligands, which has been challenging due to the reactivity and sensitivity of free carbones.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Yi-Siang Wang, Chun- Wang, Chou-Hsun Yang, Chao-Ping Hsu
Summary: This work utilizes molecular dynamic simulations and machine-learning models to investigate dynamic disorder in the coupling of hole transfer. The results demonstrate that low-frequency modes dominate these dynamics, primarily resulting from intermolecular movements such as rotation and translation. Additionally, the coupling exhibits sub-Ohmic behavior in its spectral density character, with cut-off frequencies around 10(2) cm(-1).
JOURNAL OF CHEMICAL PHYSICS
(2023)
Article
Chemistry, Physical
Wei-Ni Wu, Kei-ichiro Sato, Jun-Hao Fu, Yi-Tsu Chan, Jhih-Min Lin, Shih-Huang Tung, Tomoya Higashihara, Cheng-Liang Liu
Summary: This study systematically investigates the effects of vinyl linkers in polythiophene-based semiconductors on their structural properties, thin film morphologies, and thermoelectric performance. The introduction of vinyl groups enhances the miscibility with the dopant and improves the doping efficiency, resulting in higher electrical conductivity and power factor.
JOURNAL OF MATERIALS CHEMISTRY A
(2023)
Article
Chemistry, Inorganic & Nuclear
Kaixiu Li, Jian Huang, Shi-Cheng Wang, Zhengguang Li, Jun Wang, Yiming Li, Mingzhao Chen, Yi-Tsu Chan, Die Liu, Pingshan Wang
Summary: A terpyridine-based supramolecular cage was synthesized by the self-assembly of a hexapodal metal-organic ligand with Zn2+. The cage exhibited large parallel planes with a diameter close to 6 nm and a face-to-face distance close to 3.5 nm, and it possessed a large cavity. Various spectroscopic techniques and microscopy measurements supported the formation of the supramolecular cage. Furthermore, the corresponding metal-organic gel showed good adsorption performance for dye molecules.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Lipeng He, Lijie Li, Shi-Cheng Wang, Yi-Tsu Chan
Summary: A rational molecular design strategy is introduced for selective metal-ligand coordination, allowing for the quantitative self-assembly of heterobimetallic nano-Saturn complexes. The Cd-II ions and organometallic trans-Pt-II motifs exhibit preferential binding to specific ligands during the sequential multicomponent self-assembly. The pre-designed directive interactions enable precise control over the structural characteristics.
CHEMICAL COMMUNICATIONS
(2023)
