Article
Chemistry, Multidisciplinary
Shuo Yang, Wei-Tao Jiang, Bin Xiao
Summary: The study focused on tertiary cyclopropyl carbagermatranes obtained through zinc-mediated decarboxylation, which showed efficient reactivity in palladium-catalyzed cross-coupling reactions. They also exhibited orthogonal reactivity with boron reagents, acting as robust nucleophiles for the synthesis of tertiary cyclopropane and efficient intermediates for quaternary center formation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Hui-Qing Geng, Wenbo Li, Yanying Zhao, Xiao-Feng Wu
Summary: In this communication, a new strategy for the synthesis of diborylated cyclopropanes via a copper-catalyzed carbonylation process was introduced. The strategy showed high yields and complete diastereoselectivity. The obtained products were further transformed to demonstrate their utility in organic synthesis.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Maruti Mali, Gangavaram V. M. Sharma, Subhash Ghosh, Thierry Roisnel, Bertrand Carboni, Fabienne Berree
Summary: A Simmons-Smith stereodefined procedure for the synthesis of cyclopropyl-1,2-bis(boronates) starting from alkenes has been developed. The resulting compounds were then subjected to regioselective Suzuki-Miyaura couplings to produce diversely substituted arylcyclopropanes in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Marta Papis, Camilla Loro, Michele Penso, Gianluigi Broggini, Francesca Foschi
Summary: The synthesis of modified morpholino monomers was achieved through condensation reactions under Lewis acid conditions, utilizing a simple and efficient method to access diversified optically pure morpholino monomers with high yields and anomeric ratios.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Polymer Science
Aihemaiti Kayishaer, Mattia Annatelli, Chloe M. Hansom, Louis M. M. Mouterde, Aurelien A. M. Peru, Fabio Arico, Florent Allais, Sami Fadlallah
Summary: This study focuses on the synthesis of fully renewable polycarbonates using cellulose-based platform molecules. A solvent-free polymerization approach is utilized to obtain unique bio-based polycarbonates with high molecular weight and structural changes, paving the way for the development of functional materials with tunable properties.
MACROMOLECULAR RAPID COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Martin Jaeger Pedersen, Christian Marcus Pedersen
Summary: A method for introducing dimethylphenylsilyl at the 4-position in carbohydrates has been developed, showing higher reactivity compared to the corresponding 4-deoxy-analogue. The introduction of a C-Si increases the relative reactivity by a modest factor of around two.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Jun Cao, Stephane P. Vincent
Summary: A general methodology for preparing phosphonylated 1-spirocyclopropyl analogues of glycosyl-1phosphates is reported. The reaction showed stereospecificity, with cis/trans selectivity depending on the E/Z configuration of the starting exo-glycal. Four different spirocyclopropyl ribose-1-phosphonate isomers could be prepared in a controlled manner.
Review
Polymer Science
Melissa K. Stanfield, Rhiannon S. Terry, Jason A. Smith, Stuart C. Thickett
Summary: This review focuses on the use of levoglucosan (LGA) and levoglucosenone (LGO) obtained from cellulose pyrolysis in materials synthesis. It presents various types of polymers, including polyesters, polysaccharides, metathesis-based polymers, and photopolymerized thermosets. The sustainability and environmental impact of these syntheses are also discussed.
Article
Chemistry, Multidisciplinary
Anindita Bhowmick, Abhijit Chatterjee, Sidharth S. Pathak, Ramakrishna G. Bhat
Summary: A straightforward and practical method has been developed to synthesize alpha-substituted glutaric diesters directly from acrylates and aldehydes using visible light and Eosin Y as catalysts for hydrogen atom transfer and Giese-type addition. This method has also been explored for the preparation of substituted 4,5-dihydro-2H-pyridazinones, which have potential applications in biology and industry.
CHEMICAL COMMUNICATIONS
(2023)
Article
Materials Science, Paper & Wood
Feixiang Xu, Jiangchen Luo, Liqun Jiang, Zengli Zhao
Summary: This study improved the production of levoglucosan and levoglucosenone from acid-impregnated cellulose through fast pyrolysis. The impregnation of acid reduced the activation energy and reaction temperature, significantly increasing the yield of levoglucosan. The study demonstrated the potential for industrial production of levoglucosan and levoglucosenone from cellulose at low temperatures.
Article
Chemistry, Organic
Jan Eric Neuburger, Alina Gazizova, Sven Tiedemann, Jan von Langermann
Summary: This study demonstrates a straightforward synthesis process to prepare substituted 1,2-amino alcohols from readily available aromatic methyl ketones. The reaction involves bromination, hydrolysis, and enzymatic conversion, resulting in a high yield and excellent enantiomeric excess. Interestingly, a keto-enol-tautomerism reaction leads to an unexpected isomer of the amino alcohol.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Agricultural Engineering
Guangchuan Tang, Xin Huang, Anbang Xu, Zhongqing Yang, Changlei Qin, Jingyu Ran
Summary: This study conducted liquid-phase continuous conversion of LGA using SO3H functionalized resin to produce LGO as a bio-renewable platform for fine and commodity chemicals. The highest LGO yield of 38.4% was obtained under optimized conditions. Additionally, the use of bio-oil as substrate promoted LGO yield to 55.4%.
INDUSTRIAL CROPS AND PRODUCTS
(2022)
Article
Biochemistry & Molecular Biology
Davide Moi, Maria Chiara Cabua, Viktoria Velichko, Andrea Cocco, Annalisa Chiappone, Rita Mocci, Stefania Porcu, Monica Piras, Stefano Bianco, Fabio Pesciaioli, Francesco Secci
Summary: A straightforward continuous-flow method for the synthesis of cyclopropyl carbaldehydes and ketones has been developed using 2-hydroxycyclobutanones and aryl thiols. Under mild conditions, multigram quantities of cyclopropyl adducts can be easily obtained with the aid of acid-catalysis and reusable Amberlyst-35 as a catalyst. The physical-chemical properties of the packed bed and the continuous-flow system were characterized in detail through various analyses.
Article
Chemistry, Organic
Zeina Neouchy, Jan Hullaert, Jonas Verhoeven, Lieven Meerpoel, Jan-Willem Thuring, Guido Verniest, Johan Winne
Summary: A method for synthesizing cyclopropyl pinacol boronic esters from di-bromocyclopropanes via Matteson-Pasto rearrangement is reported. The method is scalable and exhibits limited levels of stereoinduction, with a selectivity that complements existing stereoselective borylcyclopropanation strategies. It can be utilized to rapidly access interesting building blocks for diversely functionalized cyclopropanes.
Article
Chemistry, Organic
Wenxing Wang, Shuo Zhang, Guang Shi, Zhiwei Chen
Summary: An electrochemical method was developed for synthesizing 1,2,4,5-tetrasubstituted imidazoles under undivided electrolytic conditions. This method utilizes electrochemical C(sp(3))-H amination via enamines and amines, using readily available starting materials and avoiding the use of transition metals and oxidants. The method is practical due to its broad substrate adaptability and ability to provide a simple green pathway for synthesizing GABA(A) receptor analogs.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Plant Sciences
Nicholas J. Sadgrove, Ian R. H. Telford, Guillermo F. Padilla-Gonzalez, Ben W. Greatrex, Jeremy J. Bruhl
PHYTOCHEMISTRY LETTERS
(2020)
Article
Plant Sciences
Dane Lyddiard, Theo Ozga, Ben W. Greatrex
PHYTOCHEMISTRY LETTERS
(2020)
Article
Plant Sciences
Nicholas J. Sadgrove, Guillermo F. Padilla-Gonzalez, Alison Green, Moses K. Langat, Eduard Mas-Claret, Dane Lyddiard, Julian Klepp, Sarah V. A. -M. Legendre, Ben W. Greatrex, Graham L. Jones, Iskandar M. Ramli, Olga Leuner, Eloy Fernandez-Cusimamani
Summary: Endemic desert shrubs in Australia, particularly species from the Eremophila genus, exhibit rich chemical diversity with many compounds yet to be described. Research indicates high variability in chemical composition among species within the genus, with classification based on the expression of different compounds.
Review
Chemistry, Multidisciplinary
Jason E. Camp, Ben W. Greatrex
Summary: This review discusses the conversion of levoglucosone (LGO) into biologically active compounds and future research directions related to this platform molecule.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Julian Klepp, Thomas Bousfield, Hugh Cummins, Sarah V. A-M Legendre, Jason E. Camp, Ben W. Greatrex
Summary: This paper reports a novel aldol/Michael cascade reaction, which involves the reactions of aromatic aldehydes and levoglucosenone promoted by methoxide. The reaction yields bridged alpha,0-unsaturated ketones, with up to 91% yield in 14 examples. The formation of the bridged species is thermodynamically favored, except in the case of 5-methylfurfural and pyrrole-2-carboxaldehyde.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Analytical
Wawat Rodiahwati, Trevor C. Brown, Ben W. Greatrex
Summary: The use of seaweed polysaccharides as a replacement for fossil fuel-based feedstocks in fine chemical synthesis shows promise. Acid-catalyzed pyrolysis of red seaweed polysaccharide iota-carrageenan was studied using differential scanning calorimetry (DSC). DSC results revealed that sulfuric acid in a polyethylene glycol (PEG) solvent reduced the temperature of the exothermic decomposition peak by approximately 63 degrees C compared to pure polysaccharide pyrolysis. Gas chromatography/mass spectrometry analysis of the evolved products from pyrolysis showed that levoglucosenone (LGO) and furfural were the dominant compounds. The yield of LGO was 12 mg/gIC or 9.0 mol%, and the yield of furfural was 2.8 mg/gIC or 2.8 mol% when 2% w/w H2SO4 was used as a catalyst.
JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS
(2023)
Article
Chemistry, Organic
Sarah V. A. -M. Legendre, Christopher J. Sumby, Amir Karton, Ben W. Greatrex
Summary: Bifunctional thiourea/amine organocatalysts were utilized for the desymmetrization of meso-endoperoxides via the Kornblum-DeLaMare reaction, affording 4-hydroxyketones in 78-98% yields with enantioselectivity & LE;98:2. The effects of catalyst structure, solvent, and temperature were investigated. The most promising catalyst was applied for the kinetic resolution of racemic endoperoxides, resulting in enantioenriched materials (& LE;99:1er).
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Amir Karton, Ben W. Greatrex, Robert J. O'Reilly
Summary: We report that bifunctional molecules containing hydroxyl and carbonyl functional groups can undergo an effective transfer hydrogenation via an intramolecular proton-coupled hydride transfer (PCHT) mechanism. The activation energy for the PCHT reaction is strongly dependent on the length of the alkyl chain between the hydroxyl and carbonyl functional groups but relatively weakly dependent on the functional groups attached to the hydroxyl and carbonyl carbons. The hydride transfer between two carbon atoms proceeds without the need for a catalyst or hydride transfer activating agent, indicating that the intramolecular PCHT reaction provides an effective avenue for uncatalyzed, metal-free hydride transfers at ambient temperatures.
JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Chemistry, Organic
Harald Podversnik, Ian Curtis, Elsie Pieterse, Martyn Jevric, Christopher J. Sumby, Ben W. Greatrex
Summary: In this study, enamines were prepared from morpholine and piperidine and their reactions with selected electrophiles were examined. The crystalline enamines showed excellent stability and reactivity with isocyanates, isothiocyanates, and ketenes to form amides, thioamides, and cyclobutanones, respectively.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
J. Klepp, W. Dillon, Y. Lin, P. Feng, B. W. Greatrex
Article
Plant Sciences
Nicholas J. Sadgrove, Guillermo F. Padilla-Gonzalez, Ian R. H. Telford, W. Ben Greatrex, Graham L. Jones, Rose Andrew, Jeremy J. Bruhl, Moses K. Langat, Ingrid Melnikovova, Eloy Fernandez-Cusimamani
Article
Chemistry, Physical
Stuart J. Brown, Calum J. Drummond, Jessica Marchand, Sebastian M. Marcuccio, Kieran P. Stockton, Tamar L. Greaves
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2020)
Article
Infectious Diseases
Nicholas J. Sadgrove, Haytham Senbill, Ben-Erik Van Wyk, Ben W. Greatrex
Article
Microbiology
Dane Lyddiard, Ben W. Greatrex
MICROBIOLOGY AUSTRALIA
(2019)
Article
Chemistry, Multidisciplinary
Edward T. Ledingham, Ben W. Greatrex
AUSTRALIAN JOURNAL OF CHEMISTRY
(2019)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
