Review
Chemistry, Organic
Zlata Boiarska, Tommaso Braga, Alessandra Silvani, Daniele Passarella
Summary: Asymmetric allylation is an important reaction in natural product synthesis, allowing for the preparation of versatile chiral building blocks. Brown allylation has been successfully applied in the synthesis of various natural products, including macrolides and alkaloids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Shruti Goel, Mihir Khulbe, Anshul Aggarwal, Abha Kathuria
Summary: Flow chemistry is emerging as a significant technology in organic synthesis, with its miniaturized protocol and advantages of combined techniques leading to improved synthesis and preparation of heterocyclic compounds.
MOLECULAR DIVERSITY
(2022)
Article
Chemistry, Multidisciplinary
Marc Escriba-Gelonch, Jodie Bricout, Volker Hessel
Summary: The research applies circular economy principles to a flow chemistry process for synthesizing vitamin D-3, achieving efficient recycling of starting materials through a novel separation technique using acetonitrile. The study enhances material circularity metrics and demonstrates the potential for sustainable pharmaceutical production processes.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Review
Chemistry, Physical
Claudia Carlucci
Summary: This article discusses the production of biodiesel using different catalytic methods, such as acids, bases, enzymes or supercritical fluids. Continuous flow processes and microreactors provide better control over experimental variables, increasing efficiency and safety. Additionally, combining other technologies such as microwave irradiation or ultrasounds allows for automation of the production process.
Review
Biochemistry & Molecular Biology
Micol Santi, Luca Sancineto, Vanessa Nascimento, Juliano Braun Azeredo, Erika V. M. Orozco, Leandro H. Andrade, Harald Groeger, Claudio Santi
Summary: Biocatalysts have become a popular choice in the past few years, especially when applied in continuous flow systems, which are crucial for overcoming the limitations of traditional enzymatic catalysis and enabling more sustainable synthetic pathways.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Multidisciplinary
Suyong Han, Mahdi Ramezani, Patrick TomHon, Kameel Abdel-Latif, Robert W. Epps, Thomas Theis, Milad Abolhasani
Summary: This study explores the feasibility of utilizing and recovering green solvents with switchable hydrophilicity solvents, presenting an intensified continuous flow strategy and providing accurate in situ reaction monitoring and a scalable green solvent extraction route.
Article
Biochemistry & Molecular Biology
Jing Chen, Yangyang Jiang, Jialei Yan, Chao Xu, Tao Ye
Summary: The first total syntheses of cyclic depsipeptides colletopeptide A and colletotrichamide A have been achieved through a series of transformations. By constructing a cyclic tridepsipeptide derivative as a key intermediate, followed by late-stage incorporation of the mannose fragment, the synthesis of colletotrichamide A and desilylation of the common intermediate led to the confirmation of the absolute stereochemistry of the natural products.
Article
Chemistry, Organic
Katharina Roeser, Anna Scheucher, Christopher Mairhofer, Matthias Bechmann, Mario Waser
Summary: This study demonstrates the use of quaternary ammonium iodides as catalysts for the direct conversion of readily available beta-ketolactones into dihydrobenzofurans under oxidative conditions, via a decarboxylative oxidative cycloetherification sequence facilitated by an in situ formed ammonium hypoiodite species.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Rohan Volpe, Hanson Y-L Law, Jonathan M. White, Bernard L. Flynn
Summary: Directed ortho-lithiation (DoL) is an effective method for the ortho-substitution of BINOL-phosphoric acid and BINOL-N-triflylphosphoramide, allowing for rapid assembly of mono- or disubstituted BINOL-P-acids, including unsymmetrical disubstitution. Most significantly, DoL has proven to be highly effective in the diastereoselective desymmetrization of pseudo-C-2-symmetric BINOL-N-triflylphosphoramide, resulting in a chiral P-group.
Article
Chemistry, Multidisciplinary
Xinting Liang, Minjin Yoo, Tabitha Schempp, Saki Maejima, Michael J. Krische
Summary: By utilizing a series of complex synthetic methods, the key substructures of neaumycin B were successfully synthesized, which possess potent inhibitory activity against glioblastoma.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Engineering, Chemical
V. V. Banakar, S. S. Sabnis, P. R. Gogate, A. Raha, Saurabh
Summary: Traditionally, chemical industries rely on batch or semi-continuous operations, but there is an increasing trend towards developing novel reactor designs and processes based on continuous flow. Micro and milli structured reactors are applied for continuous processing, but have limitations in handling solids. Power ultrasound is proposed as a solution for intensifying crystallization and chemical synthesis in microreactors. Ultrasound-assisted continuous processes or their combination with microreactors can bring significant intensification benefits.
CHEMICAL ENGINEERING RESEARCH & DESIGN
(2022)
Article
Chemistry, Multidisciplinary
Yuma Otake, Kyohei Adachi, Yoshiaki Yamashita, Natsumi Iwanaga, Hirokatsu Sunakawa, Taiki Shamoto, Jun-ichi Ogawa, Atsushi Ito, Yutaka Kobayashi, Keiichi Masuya, Shinichiro Fuse, Daisuke Kubo, Hidenosuke Itoh
Summary: In this study, an automated continuous-flow liquid-phase peptide synthesizer was developed for the preparation of C-terminal free peptides. The synthesizer comprised an amidation unit, extraction unit, concentration unit, and control unit. The system successfully synthesized crude dipeptides and tripeptides by using a stepwise approach. The stability of the flow system was continuously monitored, and peptide synthesis was monitored using a near-infrared (NIR) sensor. This strategy enables liquid-phase continuous-flow peptide synthesis and in-line NIR monitoring of peptide-bond formation, contributing to enhanced efficiency in peptide production.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Hirotsugu Usutani, Kenji Yamamoto, Kazuki Hashimoto
Summary: Microflow chemistry is a new and efficient technology used for safe and effective medicine production. This paper demonstrates its application in the development of a manufacturing method for napabucasin, a potential treatment for colorectal and pancreatic cancers. Traditional techniques are limited in improving yields and purity due to constraints in heat/mass transfer efficiency, while microflow chemistry offers increased possibilities through precise mixing in a microchannel. The study shows proof-of-concept for scale-up production of napabucasin using microflow chemistry techniques at the kilogram scale.
Article
Chemistry, Organic
Evan Savelson, Jetze J. Tepe
Summary: This paper describes a highly divergent synthesis of the indole-oxazole scaffold via a one-pot Friedel-Crafts/Robinson-Gabriel synthesis and its successful application to the synthesis of breitfussins C, G, and H.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chao Shan, Jinping Xu, Liming Cao, Chaoming Liang, Ruihua Cheng, Xiantong Yao, Maolin Sun, Jinxing Ye
Summary: This study developed a practical continuous flow protocol for efficient synthesis of various functionalized piperidines within minutes, with high yields and enantiomeric excess. The scalability and utility of the process were demonstrated through the efficient synthesis of a drug precursor.
Review
Chemistry, Multidisciplinary
Antonella lenia Alfano, Heiko Lange, Margherita Brindisi
Summary: The formation of amide bonds is essential in organic and synthetic medicinal chemistry. In recent years, the application of flow chemistry in amide bond formation has shown significant advantages and potential for development. This review summarizes and compares various methods and discusses future needs and prospects for sustainable synthesis.
Article
Chemistry, Applied
Guido Gambacorta, Ian R. Baxendale
Summary: In this study, a continuous-flow preparation of 2-benzoxazolinone via the Hofmann rearrangement of salicylamide using trichloroisocyanuric acid as the chlorinating agent was implemented. The system was optimized to avoid solid accumulation and enable the production of large quantities of pure desired material. Additionally, a TCCA-based chlorination of 2-benzoxazolone to the corresponding 5-chloro derivative was carried out under batch conditions.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Multidisciplinary
Pia Mueller, Adam D. Clayton, Jamie Manson, Samuel Riley, Oliver S. May, Norman Govan, Stuart Notman, Steven Ley, Thomas W. Chamberlain, Richard A. Bourne
Summary: The study compared the performance of four different multi-objective optimisation algorithms in chemical reaction optimisation, finding that EIMEGO achieved the highest hypervolume with the lowest number of experiments, while TSEMO performed better in cases with three objectives.
REACTION CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Organic
Alexander J. Nicholls, Ian R. Baxendale
Summary: This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt, commonly known as Herz salt, using the Herz reaction. The conversions of this species to various useful adducts in medicinal and materials chemistry have been well established, but isolation examples in the literature and characterization data are limited. For the first time, this study provides mass spectrometry data for this compound and proposes a new mechanism of its formation based on new experimental observations and data.
Article
Materials Science, Multidisciplinary
Te Hu, Ian R. Baxendale, Yuchang Su, Fangjiang Li, Shaomi Duan, Yaping Zhang, Honxin Fan
Summary: Combining XRD pattern analysis with DSC curves and thermodynamic equations can optimize the preparation conditions of nanomaterials and improve the speed of the preparation scheme.
APPLIED PHYSICS A-MATERIALS SCIENCE & PROCESSING
(2022)
Article
Chemistry, Organic
Oliver M. Griffiths, Steven V. Ley
Summary: The photocatalytic generation of N-centered radicals has been employed for the synthesis of N-heterospirocycles, offering a reliable method for the construction of beta-spirocydic pyrrolidines from N-allylsulfonamides and alkenes. This study demonstrates the successful construction of various beta-spirocyclic pyrrolidines, including drug derivatives, with moderate to very good yields. Derivatization of the products and a viable scale-up procedure using flow chemistry techniques have also been achieved.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
James S. Sharley, Guido Gambacorta, Ana Maria Collado Perez, Estela Espinos Ferri, Amadeo Fernandez Miranda, Jorge Sanchez Quesada, Ian R. Baxendale
Summary: In this study, a process for the synthesis of cyclic allylic nitro compounds using greener solvent and lower cost, more robust catalyst was developed. The optimized conditions were able to selectively synthesize important fragrance intermediates such as alpha-dehydroherbac, demonstrating their scope and utility.
Article
Chemistry, Organic
James S. Sharley, Guido Gambacorta, Ana Maria Collado Perez, Estela Espinos Ferri, Amadeo Fernandez Miranda, Isabelle Fernandez Fernandez, Jorge Sanchez Quesada, Ian R. Baxendale
Summary: A new method for the oxidation of Hedione 1 to dehydrohedione 2 has been developed based on a one-pot alpha-chlorination-elimination sequence, which allows for easy scalability. The unprecedented spontaneous elimination of alpha-chloro in methanol enables the oxidation to be carried out as a one-pot protocol, eliminating the need for multiple steps/reactions. A continuous flow process utilizing sulfuryl chloride has also been demonstrated, providing a steady and safe evolution of SO2 gas during the reaction.
Article
Chemistry, Multidisciplinary
Anika Salanti, Marco Orlandi, Heiko Lange, Federica Ferruti, Luca Zoia
Summary: An analytical approach based on phenol fluorescence labeling was used to understand the phenolic group distribution in different lignin specimens. The method involved selective derivatization of lignin phenolic functionalities and analysis using gel permeation chromatography. The results provided insights into the distribution of phenolic groups in different lignins.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Agricultural Engineering
Elisabetta Alfonsi, Heiko Lange, Luc Zongo, Giovanna Poce, Massimo Sgarzi, Claudia Crestini
Summary: Salicylate and benzoate sunscreen agents were encapsulated in tannin microcapsules using a green, fast, and robust ultrasound technique. The microcapsules, obtained without cross linking agents, were fully characterized, including encapsulation efficiencies. The release kinetics of the microcapsules mimicked skin conditions and showed synergistic effects between sunscreen actives and natural tannin polyphenols, reducing the amount of synthetic sunscreens needed for sustainable and environmentally friendly UV-protection systems.
INDUSTRIAL CROPS AND PRODUCTS
(2023)
Article
Chemistry, Multidisciplinary
Pia Mueller, Aikaterini Vriza, Adam D. Clayton, Oliver S. May, Norman Govan, Stuart Notman, Steven V. Ley, Thomas W. Chamberlain, Richard A. Bourne
Summary: Automated platforms enable fast and efficient optimization of chemical systems with single and multiple objectives. In this study, we demonstrate the application of automated optimization platforms for chemical screening of sulfide oxidations in flow. The identification of unique optima for each substrate emphasizes the importance of rapid and individual experimental optimization for successful compound screening.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Multidisciplinary Sciences
James S. Sharley, Guido Gambacorta, Ana Maria Collado Perez, Estela Espinos Ferri, Amadeo Fernandez Miranda, Jorge Sanchez Quesada, Ian R. Baxendale
Summary: This article presents a dataset of spectroscopic analysis performed on starting materials, intermediates, and products related to the synthesis of Hedione. The data was collected at Durham university between October 2020 and September 2021 for the development of a preparative method to Dehydrohedione. The proton, Carbon-13, and Fluorine-19 Nuclear magnetic resonance spectra of the compounds were recorded using Varian 600 MHz and Bruker Avance-40 0 instruments. The IR spectra were recorded using a Perkin Elmer Spectrum Two UATR Two FT-IR instrument, and accurate mass measurement was performed using a Waters QtoF premier mass spectrometer.
Article
Chemistry, Multidisciplinary
Samuel L. Bourne, Franz Amann, Steven V. Ley
Summary: This article provides an overview of the factors contributing to the rise of flow chemistry in the pharmaceutical industry over the past two decades. It highlights the challenges faced by the industry and how scientific progress has helped to overcome them. Current trends and examples of progress at CARBOGEN AMCIS are discussed, giving a speculative glimpse into the future of drug development and manufacturing.
Article
Engineering, Chemical
Sandro Stucki, Heiko Lange, Christopher H. Dreimol, Yves Weinand, Ingo Burgert
Summary: The moisture resistance of friction-welded wood joints can be improved by applying bio-based bonding additives. Kraft lignin showed significantly increased moisture stability after 24 h water immersion, with an average wet bond strength of 1.5 MPa. However, modification of kraft lignin through succinylation, acetylation or depolymerization did not further improve moisture stability, and depolymerized kraft lignin actually led to a higher delamination rate during water immersion. Structural and chemical analyses showed the impact of various lignin variations on thermal behavior and intermolecular interactions.
JOURNAL OF ADHESION SCIENCE AND TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Ricardo Labes, Julio C. Pastre, Richard J. Ingham, Claudio Battilocchio, Henrique M. Marcon, Mariana C. F. C. B. Damiao, Duc N. Tran, Steven V. Ley
Summary: This study reports the rapid synthesis of 2-pyrazolines from aldehydes via [3 + 2] cycloaddition of unstabilised diazo species and mono and di-substituted alkenes. The development includes semi-continuous and fully continuous methods, with a fully automated compound library generation and a graphical interface for automation control.
REACTION CHEMISTRY & ENGINEERING
(2023)
