Article
Chemistry, Organic
Xi Xiao, Xiaobiao Lu, Ming Zhang, Haoqing Hou, Changfeng Wan, Jinbiao Liu
Summary: A novel synthetic method was successfully developed for the preparation of multisubstituted dihydrochromeno[2,3-b]indole derivatives in moderate to high yields using a catalytic environmentally benign iron salt.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Haipeng Hu, Xin Wu, Yuqian Qiu, Cuilin Wang, Wei Wang, Guizhou Yue, Hanguang Wang, Juhua Feng, Guangtu Wang, Hailiang Ni, Ping Zou
Summary: In this study, the dehydrative mono-/dialkylation reactions of alcohols and beta-ketoacids were achieved under arylboronic acid catalysis, leading to the formation of beta-aryl ketones and beta-ketoesters in moderate to high yields. The reaction temperature was found to control the selectivity between decarboxylative alkylation and decarboxylation processes. A possible catalytic cycle was proposed based on experimental evidence.
Article
Chemistry, Organic
Cheng Huang, Zhifei Zhao, Shiwu Li, Jixing Zhao, Leifang Wu, Chengzhi Gu
Summary: A highly enantioselective conjugate addition has been developed for the reaction between indolizine and its analogues with alpha,beta-unsaturated 2-acyl imidazoles. This method provides excellent yields and enantioselectivities, overcoming the limitations of organocatalysts in controlling stereoselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Takanori Shibata, Mio Sasaki, Masafumi Kojima, Mamoru Ito
Summary: The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with alpha,beta-unsaturated carbonyl compounds proceeded with high enantioselectivity, yielding chirally functionalized pyrroles and indoles as formal C-H conjugate adducts. The reaction mechanism was further investigated through deuterium labeling experiments.
Article
Chemistry, Organic
Yifei Qu, Xiaojia Cai, Yuzhuang Guan, Jiamin Tan, Zhangping Cai, Minyun Liu, Yasi Huang, Jinhui Hu, Wen-Hua Chen, Jia-Qiang Wu
Summary: A facile and straightforward method for the successful synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes, and indole-3-methanamines by a Friedel-Crafts reaction is developed, showing good to excellent yields, broad substrate compatibility, good functional group tolerance, and scalability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Applied
Yanshun Li, Mengqi Dong, Nanxing Gao, Guorui Cao, Dawei Teng
Summary: A zinc complex of a new spiroQuinox ligand with a spirocarbon stereogenic center was used for asymmetric Friedel-Crafts alkylation of indoles with cyclic N-sulfonyl ketimino esters. This catalytic system allows for facile synthesis of benzosultam derivatives functionalized with indole substituents, with high yield and excellent enantioselectivity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shuang-Liang Liu, Liming Zhou, Shaoming Fang, Ru Zhao, Menglong Li, Haoran Yang
Summary: The Rh(III)-catalyzed addition of indole C2-H bond to nitroalkenes at room temperature and atmospheric pressure is reported, providing a convenient method for the synthesis of a wide range of 2-(2-nitroalkyl)indoles in high yield and selectivity. Pyrrole derivatives were also successfully employed in the Friedel-Crafts alkylation reaction. The obtained nitroalkane products could be further transformed into structurally diverse and valuable indole derivatives. Control experiments were conducted and a plausible mechanism was proposed.
Article
Chemistry, Organic
Peng Zhu, Yi Yang, Yan Liu, Yungui Peng
Summary: A series of trifunctional BINAP-based monophosphonium phase-transfer catalysts were developed and used for the asymmetric addition of alpha-diazomethylphosphonates. The method showed high tolerance for 2-unsubstituted sulfonylindoles and achieved high enantioselectivity.
Article
Biochemistry & Molecular Biology
Mohammad Shahidul Islam, Abdullah Saleh Alammari, Assem Barakat, Saeed Alshahrani, Matti Haukka, Abdullah Mohammed Al-Majid
Summary: Five new C-2-symmetric chiral ligands were synthesized from enantiopure amino alcohols, and used for Friedel-Crafts asymmetric alkylation. The bis(oxazolinyl)thiophene ligands showed higher efficiency in inducing asymmetric alkylation compared to bis(imidazolinyl)thiophene analogues.
Article
Chemistry, Organic
Pan Tang, You -Yuan Wei, Long Wen, Hao-Jie Ma, Yi Yang, Yan Jiang
Summary: This article investigates the MgI2-catalyzed nucleophilic ring-opening reactions of donor-acceptor cyclopropanes with indoline-2-thiones as sulfur nucleophiles. Under mild reaction conditions, a series of functionalized gamma-indolylthio butyric acid derivatives are obtained in good to excellent yields. Additionally, the thioether functionalized ring-opening products can be transformed into sulfone and methionine analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Shelby M. Anderson, Marcus D. Van Engen, Paul E. Floreancig
Summary: The sequential allylic alcohol transposition, carbonyl group trapping, oxocarbenium ion formation, and nucleophilic addition result in ring formation and serve as a fragment-coupling and stereocenter-generating reaction. Balancing the kinetics of productive and unproductive steps is crucial for successful applications, and solvent changes can be used to expand the scope and change the stereochemical outcomes of the processes. Mechanistic studies provide insight into the transformations and reactive species generated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Physical
Reuben B. Leveson-Gower, Gerard Roelfes
Summary: Friedel-Crafts alkylation and acylation reactions are important in synthetic and industrial chemistry. Researchers have expanded the application of these reactions through directed evolution and created bio-hybrid catalysts. This review summarizes these efforts and discusses future routes for more efficient and benign Friedel-Crafts reactions.
Article
Chemistry, Organic
Juan J. Rojas, Elena Torrisi, Maryne A. J. Dubois, Riashat Hossain, Andrew J. P. White, Giovanni Zappia, James J. Mousseau, Chulho Choi, James A. Bull
Summary: This paper reports a method for synthesizing 1,4-dioxanes and explores the catalytic mechanism of the reaction. The reaction exhibits high regio- and diastereoselectivity, and the resulting products serve as interesting motifs for drug discovery.
Article
Chemistry, Multidisciplinary
Jia-Qi Wu, Xin-Yuan Wu, Jian-Mei Lu, Qian Shi, Li-Xiong Shao
Summary: In this study, a novel La(III)-based two-dimensional metal-organic framework was synthesized and used as an efficient Lewis acid catalyst for the Friedel-Crafts alkylation reaction. The catalyst exhibited a unique structure, good stability and catalytic activity in acidic and basic environments.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Physical
Louise R. Smith, Mala A. Sainna, Mark Douthwaite, Thomas E. Davies, Nicholas F. Dummer, David J. Willock, David W. Knight, C. Richard A. Catlow, Stuart H. Taylor, Graham J. Hutchings
Summary: The study investigated the impact of different morphologies of ceria catalysts on the distribution of reaction products from glycerol solutions, finding that polyhedral ceria samples exhibited the highest methanol production. Surface area and acidity were identified as factors contributing to low glycerol conversion over cubic ceria. Rodlike and polyhedral catalysts produced a major intermediate, hydroxyacetone, with higher selectivity compared to cubic ceria, leading to increased methanol yields.
Article
Chemistry, Physical
Jonathan K. Bartley, Nikolaos Dimitratos, Jennifer K. Edwards, Christopher J. Kiely, Stuart H. Taylor
Summary: This article outlines the outstanding contributions of Graham Hutchings in the field of catalysis, covering a wide range of areas, with notable contributions to catalyst preparation methods for metal oxides and nanoparticles.
Article
Chemistry, Physical
Peter J. Miedziak, Samuel Pattisson, Jennifer K. Edwards, Brian Tarbit, Stuart H. Taylor, Graham J. Hutchings
Summary: In oxidation reactions involving oxygen as the terminal oxidant, autocatalysis can play a significant role under certain conditions, influencing reaction pathways and product formation. The initial reaction in some oxidation processes may be non-radical, but subsequent steps could involve radical processes. The impact of autocatalysis reactions varies depending on the reaction conditions.
Article
Chemistry, Physical
Tongqi Ye, James H. Carter, Bao Chen, Xin Li, Yuewen Ye, Stuart H. Taylor, Graham J. Hutchings
Summary: The oxidative dehydrogenation of propane to propene using carbon dioxide is a promising new synthesis route. Iron-chromia catalysts prepared by sol-gel exhibited high activity and a high concentration of acid and base sites. Despite some coking observed, the initial activity can be restored through oxidative regeneration.
CATALYSIS COMMUNICATIONS
(2022)
Review
Chemistry, Multidisciplinary
James W. M. Crawley, Isla E. Gow, Naomi Lawes, Igor Kowalec, Lara Kabalan, C. Richard A. Catlow, Andrew J. Logsdail, Stuart H. Taylor, Nicholas F. Dummer, Graham J. Hutchings
Summary: The development and application of trimetallic nanoparticles are rapidly accelerating in the field of catalysis, presenting exciting opportunities. Current methods for design, synthesis, analysis, and application of trimetallic nanoparticles have been explored, but challenges in controlling elemental segregation and identifying influential characteristics remain. The multielement composition of trimetallic nanoparticles exhibits beneficial synergy in oxidation, dehydrogenation, and hydrogenation reactions, but further work is needed to maximize productivity. Computational support is crucial for experimental endeavors, and the marriage of simulation and experiment is necessary to advance this field. Clear challenges remain in identifying, making, and applying trimetallic catalysts efficiently, but the outlook is strong.
Article
Chemistry, Physical
Michael Bowker, Naomi Lawes, Isla Gow, James Hayward, Jonathan Ruiz Esquius, Nia Richards, Louise R. Smith, Thomas J. A. Slater, Thomas E. Davies, Nicholas F. Dummer, Lara Kabalan, Andrew Logsdail, Richard C. Catlow, Stuart Taylor, Graham J. Hutchings
Summary: The rise in atmospheric CO2 concentration has led to a research focus on designing catalytic routes to use CO2 as a feedstock. This study investigates the Pd/ZnO catalyst for CO2 hydrogenation and finds that it has consistent metal particle composition and activity trend regardless of different synthesis procedures and ZnO types. The study provides important insights for the discovery and design of improved catalysts for CO2 hydrogenation.
Article
Chemistry, Physical
Anna Cooper, Stan Golunski, Stuart H. Taylor
Summary: The addition of potassium to the catalyst has an impact on the relationship between NOx reduction and soot oxidation. Lower potassium loadings can promote NOx reduction without affecting soot oxidation, while higher loadings almost completely disable NOx reduction and only contribute to the activity of the catalyst in the presence of soot. At a loading of 20% potassium, the potassium phase segregates, exposing other reaction sites.
Article
Chemistry, Physical
Christopher D. Evans, Jonathan K. Bartley, Stuart H. Taylor, Graham J. Hutchings, Simon A. Kondrat
Summary: Exceptional selectivity of LaMnO3 supported Au catalysts for the oxidation of glycerol to tartronic acid is reported. The choice of metal nanoparticle influences the selectivity of the catalysts.
Review
Energy & Fuels
Louise R. Smith, Mark Douthwaite, Karl Mugford, Nicholas F. Dummer, David J. Willock, Graham J. Hutchings, Stuart H. Taylor
Summary: This article provides an update on recent advances in the catalytic production of high-value chemicals from glycerol and discusses the feasibility and challenges of this approach in the industry. The economic significance of using crude glycerol as a feedstock for chemical production is also addressed, along with suggestions for improving research impact.
Article
Chemistry, Physical
Max Tigwell, Mark Douthwaite, Louise R. Smith, Nicholas F. Dummer, David J. Morgan, Donald Bethell, Stuart H. Taylor, Graham J. Hutchings
Summary: The use of heterogeneous catalysts for glycerol conversion into lactic acid has been widely studied. Aerobic oxidation under alkaline conditions has shown to achieve the highest production rates of lactic acid. However, understanding the factors influencing the selectivity of the competing pathways remains limited, highlighting the need for further investigation.
JOURNAL OF PHYSICAL CHEMISTRY C
(2022)
Article
Chemistry, Multidisciplinary
Andrew E. Graham, Liam A. Bailey, Takudzwa Bere, Thomas E. Davies, Stuart H. Taylor
Summary: Nanoporous aluminosilicate materials catalyze the formation of furaldehyde dimethyl acetal from methanol efficiently, and this reaction can be used for the production of biofuel additives.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Review
Chemistry, Multidisciplinary
Nicholas F. Dummer, David J. Willock, Qian He, Mark J. Howard, Richard J. Lewis, Guodong Qi, Stuart H. Taylor, Jun Xu, Don Bethell, Christopher J. Kiely, Graham J. Hutchings
Summary: The direct transformation of methane to methanol at a larger scale remains challenging due to the low reactivity of methane. This review examines several promising routes to methanol and evaluates the performance targets necessary for process development. It provides critical perspectives on future operation and discusses the emergence of active heterogeneous catalysts and their reaction mechanisms.
Article
Chemistry, Physical
Parag M. M. Shah, Liam A. Bailey, Stuart H. Taylor
Summary: A series of ceria-manganese mixed metal oxide catalysts with different Ce:Mn ratios were prepared by coprecipitation, and their capabilities for total oxidation of propane and naphthalene were evaluated. The catalyst with a higher manganese content showed the highest activity, specifically Ce0.25Mn0.75Ox. Characterization techniques revealed that the high activity of Ce0.25Mn0.75Ox was attributed to the formation of phase-separated Mn-substituted ceria and Mn2O3 phases. The catalyst preparation technique also played a significant role, as the mechanochemical and urea catalysts exhibited greater activity than the carbonate coprecipitated catalyst.
Article
Chemistry, Physical
Parag M. M. Shah, Liam A. A. Bailey, David J. J. Morgan, Stuart H. H. Taylor
Summary: Iron-manganese mixed metal oxide catalysts with different Fe:Mn ratios were synthesized and evaluated for total propane oxidation. The Fe0.50Mn0.50Ox catalyst showed the highest activity due to increased surface area and the formation of a Mn2O3 phase. The choice of precipitating agent was found to affect the activity, with the hydroxide-precipitated catalysts generally being more active.
Article
Engineering, Environmental
Marvin Chavez-Sifontes, Adrian Garcia, Rut Sanchis, Clarisse Furgeaud, Alvaro Mayoral, Raul Arenal, David J. Morgan, Stuart H. Taylor, Jose Manuel Lopez, Tomas Garcia, Benjamin Solsona
Summary: The addition of niobium can significantly enhance the catalytic activity of Ir/TiO2 catalysts, resulting in the presence of abundant isolated IrOx surface species and excellent catalytic activity.
JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Xuemei Liu, Chaonan Cui, Shuoshuo Wei, Jinyu Han, Xinli Zhu, Qingfeng Ge, Hua Wang
Summary: This study presents a new strategy for designing efficient photocatalysts that can convert CO2 into hydrocarbons by utilizing synergistic catalytic sites. The findings provide a solution for the selective photocatalytic reduction of CO2 to CH4.
Article
Chemistry, Multidisciplinary
Chengxian Hu, Dan Wang, Lu Wang, Ying Fu, Zhengyin Du
Summary: A novel one-pot, three-component reaction conducted under electrochemical conditions was studied. The reaction involved 2-aminothiophenols, aldehydes, and malononitrile, using TBABF4 as an electrolyte and CuI as a catalyst. The proposed reaction mechanism suggested that CuI served as an electron relay. This method offers simplified operation, high atom economy, and mild reaction conditions.
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Tina Jeoh, Jennifer Danger Nill, Wujun Zhao, Sankar Raju Narayanasamy, Liang Chen, Hoi-Ying N. Holman
Summary: In this study, the enzymatic hydrolysis of cellulose was investigated using real-time infrared spectromicroscopy. The spatial heterogeneity of cellulose was found to impact the hydrolysis kinetics. Hydration affected cellulose ordering, and Cel7A preferentially removed less extensively hydrogen bonded cellulose.
Article
Chemistry, Multidisciplinary
Tiphaine Richard, Walid Abdallah, Xavier Trivelli, Mathieu Sauthier, Clement Dumont
Summary: An effective method of grafting functionalities onto lignin based on glycerol carbonate has been developed using an efficient nickel-catalysed telomerisation reaction. This method allows lignin to have new reactive functions and reduces the glass transition temperatures of modified lignins, thereby expanding the application range of lignin-based resins.
Article
Chemistry, Multidisciplinary
Jing Qi, Xiyan Wang, Gan Wang, Srinivas Reddy Dubbaka, Patrick ONeill, Hwee Ting Ang, Jie Wu
Summary: This study presents a green and environmentally friendly approach for the synthesis of imides using electrocatalytic oxidation with H2O as the oxygen source. The method eliminates the need for toxic or expensive oxidants and achieves high yields under mild reaction conditions. It shows broad substrate compatibility and potential for industrial applications.
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Article
Chemistry, Multidisciplinary
Juho Antti Sirvio, Idamaria Romakkaniemi, Juha Ahola, Svitlana Filonenko, Juha P. Heiskanen, Ari Ammala
Summary: This article discusses the method of using supramolecular interaction between an aromatic hydrogen bond donor and lignin to achieve rapid delignification of softwood at low temperatures.
Article
Chemistry, Multidisciplinary
Yunyan Meng, Chunxiang Pan, Na Liu, Hongjiang Li, Zixiu Liu, Yao Deng, Zixiang Wei, Jianbin Xu, Baomin Fan
Summary: A novel visible light-driven synthesis method for 2,3-diamines has been developed, which has mild conditions, avoids the use of metal reagents, and can synthesize diamines and diols in one pot.
Article
Chemistry, Multidisciplinary
Mingqing Huang, Haiyang Huang, Mengyao You, Xinxin Zhang, Longgen Sun, Chao Chen, Zhichao Mei, Ruchun Yang, Qiang Xiao
Summary: A direct air-oxidized strategy for the synthesis of benzo[b]phosphole oxides was developed in this study. Arylphosphine oxides were transformed into phosphinoyl radicals, which were further combined with various alkynes to achieve the desired products. DFT calculations revealed the mechanism of phosphinoyl radical formation.
Article
Chemistry, Multidisciplinary
Anwei Wang, Jiayin Huang, Chunsheng Zhao, Yu Fan, Junfeng Qian, Qun Chen, Mingyang He, Weiyou Zhou
Summary: This study demonstrates an innovative strategy for the aerobic oxidation of C(sp(3))-H bonds using gamma-valerolactone. By optimizing the reaction conditions and utilizing specific catalysts, efficient oxidation of C(sp(3))-H bonds is achieved with good chemoselectivity in certain cases.
Article
Chemistry, Multidisciplinary
Shun Li, Likai Tong, Zhijian Peng, Bo Zhang, Xiuli Fu
Summary: Sulfide compounds show promise as electrocatalysts for water splitting, but their performance is limited by factors such as limited active sites and hindered substance transport. This study successfully prepared a high-entropy sulfide (ZnCoMnFeAlMg)(9)S-8, which reduced grain size and increased specific surface area, enabling the realization of a dual-functional catalyst with multiple catalytic sites. High entropy also modulated the electronic properties of sulfides, reducing the potential energy barrier for hydrolysis. This research introduces a new approach for functionalizing high entropy nanomaterials and improves the performance of water splitting catalysts.
