Article
Chemistry, Multidisciplinary
Zeyu Feng, Lucas Riemann, Zichen Guo, David Herrero, Martin Simon, Christopher Golz, Ricardo A. A. Mata, Manuel Alcarazo
Summary: The lack of suitable methodologies in the past has hindered the evaluation of the pentafluorocyclopropyl group as a chemotype in crop protection and medicinal chemistry. In this study, a gram-scale synthesis of an unprecedented sulfonium salt was reported, which serves as a versatile reagent for the photoinduced C-H pentafluorocyclopropylation of non-previously functionalized (hetero)arenes through a radical mediated mechanism. The protocol developed demonstrates the scope and potential benefits of introducing the pentafluorocyclopropyl unit into biologically relevant molecules and widely used pharmaceuticals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Riya Halder, Tobias Ritter
Summary: F-18-fluorination is an important and rapidly growing field in organic synthesis that has attracted significant attention from chemists. This manuscript presents a biased perspective on recent advances in the field, with a focus on the author's own chemistry, and discusses challenges for the development of new chemistry with potential impact on imaging. The aim is to provide a useful guide for chemists to develop reliable reaction chemistry suitable for radiofluorination to make a real impact on human health.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kazuho Ban, Keisuke Imai, Shuki Oyama, Jin Tokunaga, Yui Ikeda, Hiromasa Uchiyama, Kazunori Kadota, Yuichi Tozuka, Shuji Akai, Yoshinari Sawama
Summary: In this study, a novel concept for preparing deuterated reagents was established and the deuterium kinetic isotope effects were demonstrated for the first time. This research has significant implications for drug discovery based on deuterium chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Zeyu Feng, Xavier Marset, Jaime Tostado, Johannes Kircher, Zhijie She, Christopher Golz, Ricardo A. A. Mata, Martin Simon, Manuel Alcarazo
Summary: This manuscript describes the synthesis and structure of a novel sulfonium salt, 5-(trifluorovinyl)dibenzothiophenium triflate, and its utility as a versatile reagent for introducing the bioisosteric 1,1,2-trifluoroethylene linker in drug-like molecules. The developed protocol involves the reaction of this compound with alcohols and phenols to obtain a complete set of 1,2,2-trifluoro-2-(alkoxy-/aryloxy)ethyl sulfonium salts, which are purified and characterized. The subsequent single electron reduction generates the corresponding fluoroalkyl radicals that can react intra- or intermolecularly with (hetero)arenes. The conformational consequences of the CF2-CHF tether are evaluated using theoretical calculations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Xiao-Yue Chen, Ya-Ning Li, Yichen Wu, Jiahui Bai, Yinlong Guo, Peng Wang
Summary: The development of novel and reactive linchpins for carbon-carbon and carbon-heteroatom bond formation reactions has greatly contributed to the success of synthetic chemistry. This study reports the efficient synthesis of aryl sulfonium salts, a versatile electrophilic linchpin, through a novel Cu-mediated thianthrenation and phenoxathiination. Furthermore, the formal thianthrenation of arenes is achieved through the sequential Ir-catalyzed C-H borylation and Cu-mediated thianthrenation, providing a complementary method for late-stage functionalization of pharmaceuticals.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Polymer Science
Shixiong Chen, Xiaotian Zhao, Ming Jin, Wanqiu Huang, Guodong Ye, Haiyan Pan, Decheng Wan
Summary: The pyrazoline-based sulfonium salt photoacid generators showed high photosensitivity in the 365-425 nm light-emitting diode region, with efficient photolysis and high phi(+)(H) induced by intramolecular charge transfer. The energy of the S-2 orbital was significantly influenced by the heterocycles and their substituted positions, impacting the absorption spectra and quantum yield of photoacid generation.
JOURNAL OF POLYMER SCIENCE
(2021)
Review
Chemistry, Multidisciplinary
Masaaki Komatsuda, Junichiro Yamaguchi
Summary: Fluorine-containing molecules have garnered significant interest in various scientific fields for their unique properties. Efforts have been made to develop efficient fluorination reactions, expanding the scope of substrates and controlling regioselectivity/stereoselectivity. Ring-opening fluorination provides an effective method to construct complex fluorine-containing molecules from simple cyclic compounds. This review focuses on recent advancements in ring-opening fluorination, particularly with larger-sized cyclic compounds, which offer efficient access to fluorine-containing compounds that are challenging to synthesize using conventional methods.
Article
Radiology, Nuclear Medicine & Medical Imaging
Sang Hee Lee, Nunzio Denora, Valentino Laquintana, Giuseppe Felice Mangiatordi, Angela Lopedota, Antonio Lopalco, Annalisa Cutrignelli, Massimo Franco, Pietro Delre, In Ho Song, Hye Won Kim, Su Bin Kim, Hyun Soo Park, Kyungmin Kim, Seok-Yong Lee, Hyewon Youn, Byung Chul Lee, Sang Eun Kim
Summary: The new TSPO ligand [F-18]BS224 demonstrated high affinity and selectivity, allowing it to identify abnormal TSPO expression in neuroinflammation independent of the rs6971 polymorphism, indicating potential clinical utility.
EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING
(2021)
Article
Chemistry, Organic
Karlis-Eriks Krikis, Irina Novosjolova, Anatoly Mishnev, Maris Turks
Summary: A new method utilizing 1,2,3-triazoles as leaving groups in SNAr-Arbuzov reactions to transform C-N bonds into C-P bonds was developed. C6-phosphonated 2-triazolylpurine derivatives were synthesized for the first time with yields reaching up to 82% in the C-P-bond-forming event. The regioselectivity pattern of C6-position being more reactive towards substitution in the SNAr-Arbuzov reaction of 2,6-bistriazolylpurines was conclusively proven through X-ray analysis.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Engineering, Environmental
Raquel Magri, Caroline Gaglieri, Rafael Turra Alarcon, Gabriel Iago dos Santos, Gilbert Bannach
Summary: This study developed biomass-derived materials with hardened mechanical properties using patau & aacute; oil and benzophenone dianhydride. The crosslinking process utilized crosslinker and ammonium salts as catalysts. The final material exhibited high conversion rates and low water absorption.
JOURNAL OF POLYMERS AND THE ENVIRONMENT
(2023)
Article
Chemistry, Organic
Dace Cirule, Irina Novosjolova, Erika Bizdena, Maris Turks
Summary: A new approach was developed for the synthesis of C6-substituted 2-triazolylpurine derivatives, resulting in a series of products with up to 87% yields obtained through SNAr reactions. The study demonstrates the ability of the 1,2,3-triazolyl ring at the C6 position of purine to act as an effective leaving group.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biotechnology & Applied Microbiology
Biying Li, Ziqi Qiu, Jiale Huang, Xiaoling Xian, Xiaojie Zheng, Xiaoqing Lin
Summary: This study investigates the use of deep eutectic solvents (DESs) with a hydrophobic aromatic ring structure to enhance the removal of lignin from sugarcane bagasse. The results show that an increase in the number of aromatic rings may decrease the efficiency of delignification. However, the use of TEBAC:LA-based DESs proved to be highly effective in lignin removal and cellulose recovery. Comprehensive structural analyses provided valuable insights into the deconstruction process facilitated by different combinations of hydrogen bond donors and acceptors within the DES pretreatment.
FERMENTATION-BASEL
(2023)
Article
Chemistry, Physical
Guoshu Xie, Bela Torok
Summary: In this study, supported rhodium catalysts were screened for their ability to catalyze the one-step hydrogenation of various functional groups. The results demonstrate that 5% Rh/Al2O3 and 5% Rh/C showed good control over selective hydrogenation under specific time and temperature conditions. Partial and full hydrogenation were achieved by adjusting the reaction time or temperature. The applicability of this method was further demonstrated by successfully hydrogenating C=C double bonds of arenes, which is considered challenging. Importantly, the use of an Al-H2O system for in situ hydrogen production and the high, controllable selectivity make this protocol environmentally friendly and highly efficient.
Editorial Material
Biochemistry & Molecular Biology
Cohn J. McGinnity, Erik Arstad, Katherine Beck, David J. Brooks, Jonathan P. Coles, John S. Duncan, Marian Galovic, Rainer Hinz, Ella Hirani, Oliver D. Howes, Paul A. Jones, Matthias J. Koepp, Feng Luo, Daniela A. Riano Barros, Nisha Singh, William Trigg, Alexander Hammers
ACS CHEMICAL NEUROSCIENCE
(2019)
Article
Oncology
Patrick N. McCormick, Hannah E. Greenwood, Matthias Glaser, Oliver D. K. Maddocks, Thibault Gendron, Kerstin Sander, Gayatri Gowrishankar, Aileen Hoehne, Tong Zhang, Adam J. Shuhendler, David Y. Lewis, Mathias Berndt, Norman Koglin, Mark F. Lythgoe, Sanjiv S. Gambhir, Erik Arstad, Timothy H. Witney
Article
Chemistry, Multidisciplinary
Raul Pereira, Thibault Gendron, Chandan Sanghera, Hannah E. Greenwood, Joseph Newcombe, Patrick N. McCormick, Kerstin Sander, Maya Topf, Erik Arstad, Timothy H. Witney
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Endocrinology & Metabolism
Daniele Bertoglio, Jeroen Verhaeghe, Alan Miranda, Istvan Kertesz, Klaudia Cybulska, Spela Korat, Leonie Wyffels, Sigrid Stroobants, Ladislav Mrzljak, Celia Dominguez, Longbin Liu, Mette Skinbjerg, Ignacio Munoz-Sanjuan, Steven Staelens
JOURNAL OF CEREBRAL BLOOD FLOW AND METABOLISM
(2020)
Article
Chemistry, Organic
Thibault Gendron, Raul Pereira, Hafsa Y. Abdi, Timothy H. Witney, Erik Arstad
Article
Multidisciplinary Sciences
Matthias Glaser, Vineeth Rajkumar, Seckou Diocou, Thibault Gendron, Ran Yan, Pak Kwan Brian Sin, Kerstin Sander, Laurence Carroll, R. Barbara Pedley, Eric O. Aboagye, Timothy H. Witney, Erik Arstad
SCIENTIFIC REPORTS
(2019)
Article
Biotechnology & Applied Microbiology
T. W. P. Hickman, D. Baud, L. Benhamou, H. C. Hailes, J. M. Ward
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2020)
Article
Chemistry, Organic
Rachel Szpara, Alexander Goyder, Michael J. Porter, Helen C. Hailes, Tom D. Sheppard
Summary: Sugars in waste biomass are sustainable chiral building blocks for organic synthesis, especially for pharmaceutical applications of chiral saturated heterocyclic rings. A range of sugar thioacetals can be selectively dehydrated at C-2 under mild basic conditions, and the resulting ketene thioacetals can be used for the production of useful chiral building blocks through further selective dehydration reactions.
Review
Chemistry, Organic
Ismail Alahyen, Laure Benhamou, Vincent Dalla, Catherine Taillier, Sebastien Comesse
Summary: Acrylamides are versatile building blocks that can be easily obtained from common starting materials. Over the past 20 years, they have been shown to be efficient partners in domino reactions, leading to a variety of complex aza-heterocycles. Metal-free and metal-triggered reactions allow good control of the reactivity of polyvalent acrylamides, resulting in diverse synthetic outcomes.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Medicinal
Kerstin Sander, Thibault Gendron, Klaudia A. Cybulska, Fatih Sirindil, Junhua Zhou, Tammy L. Kalber, Mark F. Lythgoe, Tom R. Kurzawinski, Morris J. Brown, Bryan Williams, Erik Arstad
Summary: The study synthesized a fluorine-18 labeled aldosterone synthase inhibitor, [F-18]AldoView, and demonstrated its potential for detecting APAs in patients with PHA through imaging in mice and adrenal tissue. The tracer showed rapid distribution and clearance with binding patterns consistent with aldosterone-producing cell clusters.
JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Fatih Sirindil, Sinead Maher, Michael Scholl, Kerstin Sander, Erik Arstad
Summary: In this study, a high-yielding and robust synthetic method for accessing naked dibenzothiophenium salt precursors of complex PET tracers and their labelling with [F-18]fluoride was reported. The labelling process was found to be ultrarapid and could be conducted under mild conditions with high activity yields. This method enables facile synthesis of complex and sensitive radiotracers and can accelerate the development and clinical translation of new F-18-radiopharmaceuticals.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Isobel M. Wilson, Sandeep K. Padamati, Antonia D. Bobitan, Michael J. Porter, Katherine B. Holt
Summary: Carbon surfaces (glassy carbon, graphite, and boron-doped diamond) were functionalized with layers composed of linked pyridinium and pyridine moieties using simple electrochemical reduction of trifluoroacetylpyridinium. The functionalization process allows for rapid screening of surface properties and presents a means to test the specific catalytic performance of pyridinic groups toward key processes such as oxygen and CO2 reduction.
Article
Chemistry, Multidisciplinary
David Branquet, Mohamed Vall Sidi Boune, Nicolas Hucher, Catherine Taillier, Vincent Dalla, Sebastien Comesse, Laure Benhamou
Summary: An iron-catalysed transfer hydrogenation method has been developed for the oxidation of aldo-hexoses and -pentoses into sugar lactones using different acceptors. The transformation shows complete chemo-selectivity for the anomeric position on unprotected sugars. The method has been applied for the competitive oxidation of pentose from a mixture of C5 and C6 sugars, and the oxidation of xylose with only an equimolar amount of a carefully chosen acceptor, significantly improving the sustainability of the transformation without compromising the equilibrium shift.
Article
Chemistry, Medicinal
Thibault Gendron, Gianluca Destro, Natan J. W. Straathof, Jeroen B. Sap, Florian Guibbal, Charles Vriamont, Claire Caygill, John R. Atack, Andrew J. Watkins, Christopher Marshall, Rebekka Hueting, Corentin Warnier, Veronique Gouverneur, Matthew Tredwell
Summary: In this study, a fully automated cassette-based synthesis of [F-18]FMZ that is Good Manufacturing Practice (GMP) compatible was developed, allowing for the production of multi-patient doses of [F-18]FMZ. The synthesis process was efficient and reproducible at multiple sites, meeting quality control standards necessary for human use.
EJNMMI RADIOPHARMACY AND CHEMISTRY
(2022)
