Article
Chemistry, Multidisciplinary
Dimitrije Djukanovic, Maximilian A. Ganiek, Kohei Nishi, Konstantin Karaghiosoff, Kazushi Mashima, Paul Knochel
Summary: A new convenient method for the preparation of dicarbamoylzincs is reported in this study. The target compounds were obtained by reacting ZnCl2 and formamides or TMP2Zn with formamides. This method is compatible with sensitive functional groups such as esters, ketones, or nitro groups. The reaction of these dicarbamoylzincs with various functionalized allylic, benzylic, aryl, alkenyl compounds, acid chlorides, aldehydes, or enones resulted in the synthesis of polyfunctional amides in high yields. The C-13 NMR characterization of these new compounds is presented.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Lizhao Zhu, Rei Kinjo
Summary: In this study, a series of boron-containing compounds were synthesized. A novel compound 4 was successfully prepared by a sequence of reactions including substitution, ring contraction, and hydride abstraction. Furthermore, compound 4 underwent reactions with azobenzene and pyridazine to afford two new compounds, 5 and 6, and also reacted with a diazo compound to yield compound 7.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Materials Science, Multidisciplinary
Misbah Asif, Hasnain Sajid, Mazhar Amjad Gilani, Khurshid Ayub, Tariq Mahmood
Summary: In this study, the static and dynamic NLO responses of pure and superhalogen doped aromatic heterocyclic monomers were investigated for the first time using density functional theory calculations. The results showed enhanced reactivity and high NLO response due to doping with superhalogens.
Article
Biochemistry & Molecular Biology
Evgenia Vaganova, Dror Eliaz, Ulyana Shimanovich, Gregory Leitus, Emad Aqad, Vladimir Lokshin, Vladimir Khodorkovsky
Summary: Cyclic 6-membered aromatic compounds like benzene and azabenzenes are light-sensitive, leading to the formation of specific compounds through photoinduced reactions. These light-induced processes produce potential applications in thermal energy-harvesting and sensor fields by forming cross-linked oligomers with unique properties.
Article
Chemistry, Applied
Lang Liu, Guojin Sun, Jun Zhang
Summary: This study presents a protocol for synthesizing 2,4,5-substituted imidazole-bearing methyl groups using A3-coupling cyclization with calcium carbide as the acetylene source, reacting with amidines and aldehydes. This methodology is characterized by several features, including the utilization of a solid alkyne source, readily accessible starting materials, and applicability to 34 examples.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Daiki Higuchi, Satoshi Matsubara, Hiroki Kadowaki, Daisuke Tanaka, Kei Murakami
Summary: Discovering new catalytic applications for metals is still an important goal in organic synthesis. A Cu-catalyzed synthesis of imidazolidine through heterocyclic recombination between aziridine and diazetidine is reported. The Cu catalyst converts diazetidine into the corresponding imine, which then reacts with aziridine to form imidazolidine. The reaction is compatible with a wide range of functional groups.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Spectroscopy
Xingping Zhang, Jiujun Wang, Yewen Juan, Hualin Yang, Wei Wei, Jing Zhao
Summary: A novel fluorescence method for the detection of phosphate anions (PO43-) was developed based on porphyrin metalation. The method showed high sensitivity and satisfactory selectivity, making it a potential technique for measuring PO43- in real samples.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2022)
Article
Engineering, Environmental
Qi Cao, Jiahui Li, Beitao Liu, Yi Zhao, Jing Zhao, Hongwei Gu, Zhiyong Wei, Fei Li, Xigao Jian, Zhihuan Weng
Summary: Recyclable materials, particularly polymers synthesized from biobased monomers, have gained significant attention due to their multifunctionality and high performance. In order to overcome the trade-off between high performance and reprocessing in traditional materials, an aromatic N-heterocycles derived from biomass functionalized with ester groups were introduced into a thermoset system. The resulting resins showed exceptional flexural strength, high glass transition temperature, flame retardancy, and acid/base resistance. Additionally, the ester groups and aromatic N-heterocycles enabled easy dissolution of the network in ethylene glycol without additional catalyst. The ability to synthesize, recycle, and reuse biobased materials bearing N-heterocycles and ester groups without losing value opens up new possibilities for closed-loop, high-performance, and versatile polymer life cycles.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Applied
Yunhao Zhou, Yue Xu, Tao Zheng, Dongliang Huang, Jianyang Chen, Yongchang Wu, Ruhuai Mei, Wenbo Ma
Summary: A copper-mediated C(sp(2))-H chalcogenation of heterocycles using readily available dichalcogenide, benzeneselenol and thiol is reported. This method exhibits scalability, good chemo- and regio-selectivity, as well as broad functional group tolerance, providing an accessible approach for the synthesis of valuable aryl chalcogenides. The chalcogenated picolinamide products can be further transformed into selenoxanthones and thioxanthone scaffolds through intramolecular cyclization via a semi-one pot process.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Paul Knochel, Kevin P. Cole
Summary: The tribute to Professor Victor Snieckus focuses on his significant contributions to the field of organic chemistry and directed ortho metalation technology.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Multidisciplinary
Dawei Yang, Mengyao Li, Xuejiao Zheng, Xu Han, Chaoqi Zhang, Jordi Jacas Biendicho, Jordi Llorca, Jiaao Wang, Hongchang Hao, Junshan Li, Graeme Henkelman, Jordi Arbiol, Joan Ramon Morante, David Mitlin, Shulei Chou, Andreu Cabot
Summary: This study proposes a method of adding copper selenide nanoparticles to the cathode of lithium-sulfur batteries to trap soluble lithium polysulfides and accelerate the reaction kinetics. By adjusting the crystal phase and defect density of the copper selenide, the electronic structure, affinity toward lithium polysulfides, and electrical conductivity can be controlled, resulting in improved battery performance.
Article
Chemistry, Applied
Huajuan Fang, Xingping Zhang, Liyuan Ma, Yao Xiao, Hualin Yang, Yu Zhou
Summary: In this paper, a fluorescence biosensor based on G-quadruplex (G4) and porphyrin metalation was developed for detection of glyphosate (GLYP). The biosensor utilized G4 to enhance the fluorescence of N-methyl-mesoporphyrin IX (NMM) and catalyze the insertion of Cu2+ into NMM. GLYP can bind to Cu2+ to inhibit NMM metalation and recover the fluorescence. The biosensor showed great application prospects for measuring GLYP with high recovery rates in agricultural products.
JOURNAL OF FOOD COMPOSITION AND ANALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Simone Ghinato, Federica De Nardi, Paola Bolzoni, Achille Antenucci, Marco Blangetti, Cristina Prandi
Summary: This paper reports a straightforward and efficient method utilizing lithium amide as a metalating agent to promote the metalation/anionic Fries rearrangements of O-aryl carbamates, under aerobic/ambient-friendly reaction conditions. This method enables the sustainable preparation of salicylamide derivatives with high levels of chemoselectivity within ultrafast reaction times, working at room temperature in the presence of air/moisture and using environmentally responsible cyclopentyl methyl ether as a solvent. Furthermore, the regioselective manipulation of O-2-tolyl carbamates has been achieved using interchangeably alkyllithiums or lithium amides, with an unexpected beneficial contribution from the utilization of biorenewable protic eutectic mixtures as non-innocent reaction media.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Inorganic & Nuclear
Francisco Reigosa-Chamorro, Luis R. Raposo, Paula Munin-Cruz, M. Teresa Pereira, Catarina Roma-Rodrigues, Pedro Baptista, Alexandra R. Fernandes, Jose M. Vila
Summary: This study demonstrated that palladacycles containing diphosphines showed selective cytotoxicity towards ovarian cancer cells, inducing apoptosis and autophagy through different pathways. While compound 3 displayed antiangiogenic effects crucial for fighting cancer progression, compound 9 promoted angiogenesis, indicating potential clinical applications for both pro- and antiangiogenic effects.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Alma Araujo Martinez, Christopher P. Landee, Diane A. Dickie, Jan L. Wikaira, Fan Xiao, Mark M. Turnbull
Summary: Three 4-(2'-pyridyl)imidazole (4-pyim) complexes of copper(II) have been synthesized and studied structurally and magnetically. Compound 1 crystallizes in the monoclinic space group P2(1)/n with a four-coordinate Cu(II) forming dimers via semi-coordinate bonds. Compound 2 crystallizes in the triclinic space group P - 1 with five-coordinate Cu(II) ions and an extensive hydrogen bonding network. Compound 3 crystallizes in the monoclinic space group Cc with both four- and five-coordinate Cu(II) ions and shows hydrogen bonding and pi-stacking interactions. Magnetic susceptibility data of compound 1 shows modest antiferromagnetic interactions best fit using a honeycomb model.
JOURNAL OF COORDINATION CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Lingaswamy Kadari, William Erb, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Dmitry Lyakhov, Thierry Roisnel, Palakodety Radha Krishna, Florence Mongin
Summary: The study involved the reaction of various substituted iodoferrocenes with acetamide under specific conditions to investigate the impact of substituents and their positions on the products. DFT calculations revealed a higher activation barrier for the oxidative addition in the ferrocene series compared to classical planar aromatics. Structure-property relationships were used to rationalize the reactivity of the different iodoferrocenes.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Min Wen, William Erb, Florence Mongin, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Thierry Roisnel, Vincent Dorcet
Summary: This study reported a general synthetic method for the functionalization of N,N-dialkylferrocenyl sulfonamides. Additionally, the ligand behavior of new ferrocene phosphines in palladium-catalyzed coupling reactions was investigated.
Article
Chemistry, Multidisciplinary
Min Wen, William Erb, Florence Mongin, Marielle Blot, Thierry Roisnel
Summary: Enantiopure ferrocene-1,2-disulfoxide derivatives have been synthesized using the rational use of directed deprotometallation, sulfur oxidation, and sulfoxide/lithium exchange. They not only represent the first members of this original family, but some of them have shown promise as ligands in rhodium-catalysed conjugate addition.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Shagor Chowdhury, Quentin Reynard-Feytis, Clement Roizard, Denis Frath, Floris Chevallier, Christophe Bucher, Thomas Gibaud
Summary: Ditopic bis-(triazole/pyridine)viologens self-assemble into coordination polymers under light irradiation, leading to mechanical and structural transitions at the macroscopic scale. Adjusting irradiation conditions can result in the formation of aggregates and gels, with aggregates being dense, polydisperse, micron-sized, spindle-shaped particles. Analysis of these states shows an arrested phase separation process, presenting a new scenario for supramolecular systems.
JOURNAL OF PHYSICAL CHEMISTRY B
(2021)
Article
Chemistry, Organic
Kmar Abaid, William Erb, Marielle Blot, Thierry Roisnel, Florence Mongin, Soufiane Touil
Summary: This article presents a method for the synthesis of ferrocenephosphonates and describes further functionalization through regioselective deprotolithiation and Negishi and Suzuki-Miyaura cross-coupling reactions. These findings provide important insights and foundations for organic synthesis and coordination chemistry.
SYNTHESIS-STUTTGART
(2022)
Article
Electrochemistry
Shaymaa Al Shehimy, Denis Frath, Elise Dumont, Floris Chevallier, Christophe Bucher
Summary: CF3-substituted porphyrins have attracted increasing interest. This study reports the synthesis of a series of free base porphyrins incorporating one, two, and three CF3 substituents, including a never-before-described 5,10,15-tris(CF3) substituted porphyrin. Detailed electrochemical and spectroscopic analyses were carried out to assess the electron-withdrawing properties of CF3 substituents compared to C6F5. The study proposes an interpretation of the unusual electrochemical signature of these molecules featuring three successive one-electron reduction waves.
Article
Biochemistry & Molecular Biology
Min Wen, William Erb, Florence Mongin, Yury S. Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Thierry Roisnel
Summary: The study aimed to design synthetic methodologies for the synthesis of polysubstituted ferrocenesulfoxides using polar organometallic reagents. By introducing a third substituent and removing specific groups, enantiopure ferrocenesulfoxides with various substitution patterns were successfully synthesized.
Article
Chemistry, Multidisciplinary
Shaymaa Al Shehimy, Orsola Baydoun, Sandrine Denis-Quanquin, Jean-Christophe Mulatier, Lhoussain Khrouz, Denis Frath, Elise Dumont, Muralee Murugesu, Floris Chevallier, Christophe Bucher
Summary: We report the synthesis and magnetic properties of a Ni(II)-porphyrin tethered to an imidazole ligand through a flexible electron-responsive mechanical hinge. The reversible folding motion of the hinge, triggered by electrical stimulation, forces the coordination of the imidazole ligand onto the Ni(II) center, resulting in a spin state change. This spin state switching, driven by pi-dimerization between viologen cation radicals, is supported by NMR, (spectro)electrochemical, and magnetic data as well as quantum calculations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Kmar Abaid, William Erb, David Virieux, Laurent Picot, Benjamin Musnier, Valerie Thiery, Thierry Roisnel, Florence Mongin, Soufiane Touil
Summary: An efficient and simple method was developed for the synthesis of unprecedented 4,5-diphosphonyldihydropyridazines and 3,4-diphosphonylpyrroles. The reactions proceeded under operationally simple, mild, and catalyst-free conditions, and showed promising growth inhibition against melanoma cancer cells.
Article
Chemistry, Organic
Loubna Elmir, Ghenia Bentabed-Ababsa, William Erb, Thierry Roisnel, Florence Mongin
Summary: When 2-iodobenzofuran was treated with lithium 2,2,6,6-tetramethylpiperidide and an aldehyde, the only isolated product was the 2-substituted 3-iodobenzofuran. However, 2-iodobenzothiophene produced mixtures of 2-substituted 3-iodobenzothiophene and 2-substituted benzothiophene under the same conditions. The use of 2-bromobenzothiophene as a catalyst reduced the competitive dehalogenation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Mohamed Hasyeoui, Peter M. Chapple, Frederic Lassagne, Thierry Roisnel, Marie Cordier, Ali Samarat, Yann Sarazin, Florence Mongin
Summary: The functionalization of methylated azines and diazines has attracted the interest of chemists due to the structural diversity it provides. Hindered lithium dialkylamides have shown chemoselectivity in deprotonating these substrates, while lithium diethylamide has been underutilized for this purpose. This article aims to review the reagents used for deprotonating methylpyridines, -quinolines, and -quinoxalines, and investigates the results obtained by functionalizing various substrates with lithium diethylamide (picolines, 2,4-lutidine, methylquinolines, and 2-methylquinoxaline). The use of an in-situ trap, namely a zinc chloride chelate, in these reactions is also discussed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Durga Golagani, Sriram Ajmeera, William Erb, Florence Mongin, Srirama Murthy Akondi
Summary: This study describes a novel ferrocene-catalyzed cyanoalkyl-imidation of aryl alkenes using cycloketone oxime esters in MeCN under redox-neutral conditions. The cycloketone oxime ester acts as a bifunctional reagent, allowing for easy access to diverse distal imido-nitriles with 100% atomic utilization. Preliminary mechanistic studies suggest that the ferrocene-ferrocenium catalytic cycle is responsible for the deconstructive functionalization of cycloketone oxime esters.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Min Wen, William Erb, Florence Mongin, Jean-Pierre Hurvois, Yury S. S. Halauko, Oleg A. A. Ivashkevich, Vadim E. E. Matulis, Marielle Blot, Thierry Roisnel
Summary: The functionalization of (R,R)-S,S'-di-tert-butylferrocene-1,1'-disulfoxide by deprotolithiation-electrophilic trapping sequences was studied, leading to polysubstituted, enantiopure derivatives with determined properties. The regioselectivity of subsequent functionalization was explained based on pK(a) values and structural data. The deprotometallation-trapping sequence allowed for the synthesis of highly substituted ferrocenes, including octa, nona, and decasubstituted derivatives. The prepared ferrocene-1,1'-disulfoxides were tested as ligands for enantioselective catalysis and their electrochemical properties were investigated.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Hang Yin, Roselyne Rosas, Stephane Viel, Michel Giorgi, Valerie Monnier, Laurence Charles, Didier Siri, Didier Gigmes, Youssef Nassar, Floris Chevallier, Christophe Bucher, Ruibing Wang, Anthony Kermagoret, David Bardelang
Summary: This article describes the structural tunability of cucurbit[8]uril (CB[8]) host/guest complexes and their responsiveness to various stimuli in water. A series of versatile 3:2 host/guest complexes were prepared by combining CB[8] with symmetric, linear diviologens, exhibiting remarkable dynamic properties and external ring translocation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Materials Science, Multidisciplinary
Vivien Andrieux, Thomas Gibaud, Julien Bauland, Thibaut Divoux, Sebastien Manneville, Stephan Guy, Amina Bensalah-Ledoux, Laure Guy, Floris Chevallier, Denis Frath, Christophe Bucher
Summary: Redox-active conductive supramolecular gels involving highly ordered chiral assemblies of small organic molecules have been synthesized and characterized in this study. The gelation process and properties of the gels were thoroughly investigated, and it was found that the optical, rheological, and electrical properties of the gels can be tuned by adding ionic additives. The self-assembly process formed chiral hollow core-shell cylinders with specific dimensions.
JOURNAL OF MATERIALS CHEMISTRY C
(2023)
