Article
Chemistry, Organic
Nan-Fang Mo, Ying Zhang, Zheng-Hui Guan
Summary: An asymmetric organocatalyzed three-component Povarov reaction has been developed to construct azaspirocycles. A chiral phosphoric acid catalyst with a unique structure was highly efficient in the reaction, leading to a wide range of azaspirocycles in high yields and excellent enantioselectivities. This reaction has expanded the scope of the traditional Povarov reaction.
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.
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
Zhimei Mao, Aimin Huang, Lin Ma, Min Zhang
Summary: A facile visible light-promoted approach has been developed for the synthesis of anthracenone-furans from readily available 2,3-dibromonaphthoquinones and phenylbenzofurans via a formal Diels Alder reaction. This reaction involves wavelength-selective agitation of 4CzIPN, energy transfer to quinones, recombination of 1,6-biradicals, and elimination to give anthracenone-furans in good to excellent yields in one pot.
Article
Chemistry, Organic
Avishek Guin, Rahul N. Gaykar, Shiksha Deswal, Akkattu T. Biju
Summary: This study demonstrates a transition-metal-free, three-component, and diastereoselective [6 + 3] annulation reaction using tropone, imino esters, and arynes to synthesize bridged azabicyclo[4.3.1]decadienes. The nitrogen ylides generated from imino esters and arynes undergo regioselective addition to tropone to produce the desired products with moderate to good yields and good functional group tolerance under mild conditions.
Article
Chemistry, Multidisciplinary
Jie Ouyang, Rajat Maji, Markus Leutzsch, Benjamin Mitschke, Benjamin List
Summary: Here, we report the design of a highly enantioselective, catalytic (4 + 3) cycloaddition reaction enabled by strong and confined IDPi Lewis acids. This reaction allows the synthesis of novel compounds with multiple stereocenters from gem-dialkyl 2-indolylalcohols and dienolsilanes. The method exhibits broad substrate scope and versatile downstream chemical modifications. Density functional theory-supported mechanistic studies reveal the significance of the in-situ generated silylium species in an overall concerted yet asynchronous cycloaddition.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Multidisciplinary
Jia-Qi Xie, Ren-Xiao Liang, Yi-Xia Jia
Summary: This review focuses on recent development of catalytic asymmetric Heck reaction and reductive Heck reaction, covering intermolecular and intramolecular versions since 2011. The article is organized in terms of the catalysts and olefin substrates, providing a clear structure for readers.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Salvador Mastachi-Loza, Tania I. Ramirez-Candelero, Luis J. Benitez-Puebla, Aydee Fuentes-Benites, Carlos Gonzalez-Romero, Miguel A. Vazquez
Summary: Chalcones are aromatic ketones that have a wide range of biological activity and are biogenetic precursors of other important molecules. Due to their structural diversity and ease of synthesis, they are often used as building blocks for chemical transformations. They can participate in nucleophilic additions and Diels-Alder reactions, and novel methodologies have been developed for [4+2] cycloadditions using chalcones as electron systems.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
David M. Malouf, Abigail D. Richardson, Scott J. L'Heureux, Elizabeth A. McDonough, Ava M. Henry, Jerry Y. Sheng, Erica A. Medhurst, Angel E. Canales, Cameron J. Fleischer, Ty B. Cecil, Spencer E. Thurman, Cameron C. McMullen, Philip J. Costanzo, Daniel A. Bercovici
Summary: In this study, Ylidenenorbornadienes (YNDs) were prepared by [4 + 2] cyclo-additions and were found to react with beta-mercaptoethanol to yield a mixture of four diastereomers. These diastereomers exhibited retro-[4 + 2] cycloaddition at different rates. The rate constants of the diastereomers were extrapolated using a simulated kinetics approach. The fragmentation of YNDs showed a wide variability in rate, depending on the stereoelectronics of the ylidene substituents. Notably, a substrate containing one carboxylic ester exhibited exceptional stability to fragmentation.
Article
Chemistry, Physical
Xiao-Qing Han, Lei Wang, Ping Yang, Jing-Yuan Liu, Wei-Yan Xu, Chao Zheng, Ren-Xiao Liang, Shu-Li You, Junliang Zhang, Yi-Xia Jia
Summary: A palladium-catalyzed intramolecular enantioselective Mizoroki-Heck reaction of naphthalenes has been developed, leading to the formation of a series of unique heterocyclic compounds with enantiomeric excess values retained. The reaction relies on the use of a chiral sulfonamide phosphine ligand to inhibit competitive and undesired reactions.
Article
Chemistry, Multidisciplinary
Anna Domzalska-Pieczykolan, Ignacio Funes-Ardoiz, Bartlomiej Furman, Carsten Bolm
Summary: Efficient protocols for selective α- and β-arylations of structurally diverse vinyl ethers were developed, showing high economic benefits and reduced waste production. Computational studies provided insights into the key factors determining the regioselectivities of the reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Anna Domzalska-Pieczykolan, Ignacio Funes-Ardoiz, Bartlomiej Furman, Carsten Bolm
Summary: This study developed simple and efficient protocols for palladium-catalyzed regioselective alpha- and beta-arylations of structurally diverse vinyl ethers. The methods are applicable to a wide range of substrates and produce low waste due to the use of limited reagents.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Gangming Xu, Suiqun Yang
Summary: Natural [4 + 2]-cyclases play a crucial role in the biosynthesis of natural products, with microbial [4 + 2]-cyclases exhibiting structural diversity and a broad substrate range. The evolutionary history and catalytic mechanisms of these cyclases, with 52 characterized so far, remain unclear.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2021)
Article
Chemistry, Organic
Subhankar Ghosh, Shital K. Chattopadhyay
Summary: In this study, a single metal catalyst and air as the oxidant were used to achieve tandem C-H arylation and C-H amidation of cis-cinnamyl hydroxamates, leading to the regioselective formation of a 3-aryl-2-quinolone ring system. Under identical conditions, the corresponding trans-isomer resulted in a 4-aryl-2-quinolone derivative. The observed complementary regioselectivity during the tandem C-H arylation and C-H amidation of isomeric substrates is unusual and has potential applications.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Masao Ohashi, Dan Tan, Jiayan Lu, Cooper S. Jamieson, Daiki Kanayama, Jiahai Zhou, K. N. Houk, Yi Tang
Summary: The synthesis of cis-decalin structures using [4 + 2] cycloaddition with high stereoselectivity is challenging. In this study, we investigated the biosynthetic pathway of the fungal natural product fischerin (1) and identified a novel pericyclase, FinI, which catalyzes this reaction. The cocrystal structure of FinI, a predicted O-methyltransferase, with the product and SAM provides valuable insights into the natural formation of cis-decalin.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Engineering, Environmental
Adam D. Clayton, Artur M. Schweidtmann, Graeme Clemens, Jamie A. Manson, Connor J. Taylor, Carlos G. Nino, Thomas W. Chamberlain, Nikil Kapur, A. John Blacker, Alexei A. Lapkin, Richard A. Bourne
CHEMICAL ENGINEERING JOURNAL
(2020)
Article
Engineering, Environmental
Connor J. Taylor, Megan Booth, Jamie A. Manson, Mark J. Willis, Graeme Clemens, Brian A. Taylor, Thomas W. Chamberlain, Richard A. Bourne
Summary: A novel kinetic modelling methodology was developed to identify the correct reaction model and kinetic parameters by an autonomous framework combined with transient flow measurements; an automated flow chemistry platform conducted linear flow-ramp experiments to map reaction profiles rapidly; computational approach discriminated between possible reaction models and identified correct kinetic parameters for each process.
CHEMICAL ENGINEERING JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Mary Bayana, A. John Blacker, Adam D. Clayton, Katherine E. Jolley, Ricardo Labes, Connor J. Taylor, William Reynolds
Summary: Continuous flow chemistry is still relatively untaught in most chemistry undergraduate courses, but by developing undergraduate projects that utilize cheap materials to construct continuous flow reactors, students can compare different types of reactors and conditions, gaining practical experience in continuous flow techniques.
JOURNAL OF FLOW CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Connor J. Taylor, Alastair Baker, Michael R. Chapman, William R. Reynolds, Katherine E. Jolley, Graeme Clemens, Gill E. Smith, A. John Blacker, Thomas W. Chamberlain, Steven D. R. Christie, Brian A. Taylor, Richard A. Bourne
Summary: Implementing statistical training into chemistry courses can enhance student learning. This paper introduces a flow chemistry laboratory practical for integrating design of experiments optimization techniques into organic chemistry experiments.
JOURNAL OF FLOW CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Connor J. Taylor, Jamie A. Manson, Graeme Clemens, Brian A. Taylor, Thomas W. Chamberlain, Richard A. Bourne
Summary: Continuous-flow aided kinetic analysis is gaining popularity due to the favorable characteristics of flow reactors, the growth of flow chemistry, and the development of innovative techniques allowing more kinetic information to be obtained using less reaction material.
REACTION CHEMISTRY & ENGINEERING
(2022)
Review
Chemistry, Multidisciplinary
Connor J. Taylor, Alexander Pomberger, Kobi C. Felton, Rachel Grainger, Magda Barecka, Thomas W. Chamberlain, Richard A. Bourne, Christopher N. Johnson, Alexei A. Lapkin
Summary: From the beginning of a synthetic chemist's training, experiments are conducted based on recipes from textbooks and manuscripts. However, it has been shown that model-based, algorithm-based, and miniaturized high-throughput techniques outperform human chemical intuition in understanding chemical systems and achieving reaction optimization. Many synthetic chemists are not exposed to these techniques, leading to a disproportionate number of scientists unable to utilize these methodologies. This review serves as a reference for inspired scientists, highlighting the basics and cutting-edge of chemical reaction optimization and its relation to process scale-up.
Article
Chemistry, Applied
Jacek Zakrzewski, Polina Yaseneva, Connor J. Taylor, Matthew J. Gaunt, Alexei A. Lapkin
Summary: Development of scalable processes for C(sp3)-H oxidative carbonylation of alkylamines provides convenient access to the beta-lactam scaffol d. The kinetics study shows that the reaction is CO-limited, and there is an optimal CO concentration for the most effective outcome, which leads to an increase in the turnover number in the optimized process. Two scalable processes, a batch process with low catalyst loading and a continuous process using a copper-tube-flow reactor, were developed. The continuous process achieved good results in oxidative carbonylation of several alkylamines without the need for optimization. This study expands the utility of flow chemistry applications to oxidative carbonylations and scalable metal-catalyzed processes.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2023)
Article
Chemistry, Multidisciplinary
Connor J. Taylor, Kobi C. Felton, Daniel Wigh, Mohammed I. Jeraal, Rachel Grainger, Gianni Chessari, Christopher N. Johnson, Alexei A. Lapkin
Summary: This study explores the use of multitask Bayesian optimization (MTBO) to accelerate the optimization of new reactions by leveraging reaction data collected from historical optimization campaigns. The methodology was successfully applied in medicinal chemistry applications, demonstrating its effectiveness in accelerating reaction optimization.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Multidisciplinary
Connor J. Taylor, Hikaru Seki, Friederike M. Dannheim, Mark J. Willis, Graeme Clemens, Brian A. Taylor, Thomas W. Chamberlain, Richard A. Bourne
Summary: The novel automated computational approach described in the report is used for chemical reaction network identification, specifically in determining kinetic models and parameters with minimal human intervention. Multiple case studies demonstrate the wide scope and applicability of this methodology, which can be applied to experimental data from any source. The open-source code for this methodology is also provided.
REACTION CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Multidisciplinary
Brendan L. Hall, Connor J. Taylor, Ricardo Labes, Alexander F. Massey, Robert Menzel, Richard A. Bourne, Thomas W. Chamberlain
Summary: An automated continuous flow reactor system with inline analysis was developed for self-optimization of a nanoparticle-catalyzed reaction, achieving maximum conversion in under 2.5 hours. Data from this optimization was used to generate a kinetic model for predicting reaction outcomes under different conditions, potentially accelerating the development timeline for emerging catalysts.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Christiane Schotten, Connor J. Taylor, Richard A. Bourne, Thomas W. Chamberlain, Bao N. Nguyen, Nik Kapur, Charlotte E. Willans
Summary: Synthetic electrochemistry has become an exciting technology for chemical synthesis, with alternating polarity frequency having a crucial impact on the observed reaction rate of Cu(i)-NHC complex formation, allowing for enhanced yield that is stable over extended reaction times.
REACTION CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Multidisciplinary
Fanfu Guan, Nikil Kapur, Louise Sim, Connor J. Taylor, Jialin Wen, Xumu Zhang, A. John Blacker
REACTION CHEMISTRY & ENGINEERING
(2020)
Review
Chemistry, Multidisciplinary
Adam D. Clayton, Jamie A. Manson, Connor J. Taylor, Thomas W. Chamberlain, Brian A. Taylor, Graeme Clemens, Richard A. Bourne
REACTION CHEMISTRY & ENGINEERING
(2019)
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)
