Article
Chemistry, Organic
Manar Ahmed Fouad, Francesco Ferretti, Simone Galie, Fabio Ragaini
Summary: In this study, formic acid was used as a surrogate for CO to successfully deoxygenate nitroarenes to nitrosoarenes, activated by acetic anhydride and a base. The nitrosoarenes were then trapped by conjugated dienes to form 3,6-dihydro-2H-[1,2]-oxazines. CuCl was employed as the catalyst to transform the oxazines into N-arylpyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Beata Gatlik, Wojciech Chaladaj
Summary: A Pd-catalyzed three-component protocol was developed for the direct synthesis of perfluoroalkyl-substituted alpha,beta-unsaturated esters using formates as convenient CO sources. The reaction proceeded smoothly under mild conditions with high yields and excellent selectivities. Detailed mechanistic studies supported by DFT calculations were conducted to understand the reaction pathway.
Article
Chemistry, Physical
Xuetong Li, Alba Villar-Yanez, Charlene Ngassam Tounzoua, Jordi Benet-Buchholz, Bruno Grignard, Carles Bo, Christophe Detrembleur, Arjan W. Kleij
Summary: We have developed a silver-catalyzed cascade conversion method for the selective formation of keto-functionalized cyclic carbonates using modular alkyne-1,n-diols and carbon dioxide. This method is characterized by its operational simplicity, excellent scope of carbonate-based heterocycles, and mild reaction conditions.
Article
Chemistry, Applied
Miguel A. Munoz-Torres, Fernando Martinez-Lara, Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The combination of organolithium chemistry with gold catalysis offers a new synthetic strategy for accessing polysubstituted indoles and carbazoles. This method utilizes ketopyrroles as starting materials and involves a series of reactions to selectively synthesize the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Dan Wang, Zhaohua Wan, Heng Zhang, Hesham Alhumade, Hong Yi, Aiwen Lei
Summary: A novel electrochemical reductive arylation method was developed for the efficient synthesis of various diarylamines without the need for transition-metal catalysts. The reaction could be scaled up efficiently in a flow cell, and several derivatization reactions were successfully carried out. Cyclic voltammetry experiments and mechanism studies revealed the roles of acetonitrile, formic acid, and triethyl phosphite in promoting this reductive arylation transformation.
Article
Chemistry, Physical
Dan Xu, Ruirui Liu, Jianfeng Li, Huacheng Zhao, Jiantai Ma, Zhengping Dong
Summary: Atomically dispersed Co catalysts with Co-N-4 active sites were successfully prepared in this study, facilitating transfer hydrogenation between nitroarenes and saturated N-heterocycles in aqueous solution. These catalysts exhibit higher TOF values compared to nanoparticle catalysts, demonstrating excellent catalytic performance.
APPLIED CATALYSIS B-ENVIRONMENTAL
(2021)
Article
Biochemistry & Molecular Biology
Sofia Siciliano, Elena Cini, Maurizio Taddei, Giorgia Vinciarelli
Summary: The synthesis of 2-substituted indoles from unprotected 2-alkynylanilines using Pd(OAc)(2) catalyst in 3% TPGS-750-M water was found to be sensitive to the heating mode and the MW delivery mode, with convectional heating often proving more effective than microwave dielectric heating. Additionally, a tandem Sonogashira-cyclisation reaction was successfully achieved in the nanomicellar water environment with Pd(OAc)(2)/Xphos.
Article
Materials Science, Multidisciplinary
Si Li, Anxiang Guan, Chao Yang, Chen Peng, Ximeng Lv, Yali Ji, Yueli Quan, Qihao Wang, Lijuan Zhang, Gengfeng Zheng
Summary: The study introduces a dual metal atomic catalyst with Cu-Cu atoms demonstrating high efficiency and selectivity in CO electroreduction to C2+ products, while the Cu-Ni atoms mainly convert CO to CH4.
ACS MATERIALS LETTERS
(2021)
Article
Multidisciplinary Sciences
Shuaishuai Wang, Tingrui Li, Chengyihan Gu, Jie Han, Chuan-Gang Zhao, Chengjian Zhu, Hairen Tan, Jin Xie
Summary: This article reports on an iron-catalyzed reaction for efficient construction of aromatic tertiary amines, which is important in drug discovery and organic chemistry. The reaction employs a radical tandem C-N coupling strategy and can synthesize nonsymmetric aromatic tertiary amines under mild conditions.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Xin-Shen Liang, Rui-Dong Li, Wei Sun, Zhong Liu, Xiao-Chen Wang
Summary: Borane-mediated hydride abstraction has been shown to be a powerful tool for the C(sp(3))-H functionalization of amines, but its activity with ethers is still unknown. In this study, we discovered this activity in 2H-chromenes and established a catalytic C(sp(3))-H functionalization reaction using silyl ketene acetals as nucleophiles.
Article
Engineering, Chemical
Zhouxin Chang, Feng Yu, Zhisong Liu, Zijun Wang, Jiangbing Li, Bin Dai, Jinli Zhang
Summary: Ni-Al mixed metal oxides catalysts prepared by high shear mixer and coprecipitation methods show excellent activity for low temperature CO methanation. The catalysts have small crystallite size and high surface area which contribute to the methanation reaction. The presence of defective oxygen accelerates the dissociation of CO and enhances the activity of the catalyst. The reaction produces CHO and COH intermediates with lower activation energy barriers and hydrogen-assisted carbon-oxygen bond scission is favorable.
CHINESE JOURNAL OF CHEMICAL ENGINEERING
(2022)
Article
Chemistry, Applied
Jiajun Wu, Satawat Tongdee, Yuvaraj Ammaiyappan, Christophe Darcel
Summary: By starting from nitroarenes and using hydrosilylation conditions with a well-defined N-heterocyclic carbene iron(0) catalyst, aniline derivatives were successfully produced in moderate to high yields. Furthermore, a selective synthesis of cyclic amines such as pyrrolidines, piperidines, and azepanes was achieved from levulinic acid, 1,5- and 1,6-keto acids, respectively, with isolated yields up to 69% under visible light irradiation and thermal conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Zhenzhen Zhou, Xiao Liu, Jian-Gong Ma, Peng Cheng
Summary: Environmental problem caused by carbon emission has attracted widespread attention. This study developed a new dual-active site catalyst for converting CO2 into formamides, which has the advantages of high efficiency, low cost, and reusability. It provides a reliable approach to unify the advantages of homogeneous and heterogeneous catalysts, and has significant implications for synthetic chemistry and environmental protection.
Article
Chemistry, Organic
Mummadi Sandeep, Bangarigalla Shantharjun, Geetala Pradeep Kumar, Kallu Rajender Reddy
Summary: A simple, mild, and efficient oxidative copper-catalyzed regioselective trifluoromethylation of imidazo[1,5-a]-N-heteroarenes has been developed. This method offers biologically relevant trifluoromethylated fused imidazoles in moderate to good yields with good functional group tolerance under mild conditions. Key features include short reaction time and room temperature reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Sami Chniti, Laszlo Kollar, Attila Benyei, Agnes Dornyei, Attila Takacs
Summary: Novel N-substituted pyrrolo[3,4-b]quinoline-1,3-diones have been synthesized successfully through a highly selective palladium-catalyzed carbonylative imidazation-cyclization reaction. This method, applied for the first time to access original scaffolds, involves 3-bromo-2-iodoquinoline as a typical partner, primary amines, and atmospheric or high carbon monoxide pressure. The use of bidentate ligands such as XantPhos and dppp in atmospheric or high-pressure conditions provides a wide range of carbonylated compounds with good to excellent yields (up to 82%). Furthermore, new quinoline-2,3-dicarboxamides have been isolated as side products in very low yields and have been fully characterized. The solid state structures of three synthesized acridinimides have been unequivocally established by single-crystal XRD analysis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ji Yang, Jiawang Liu, Yao Ge, Weiheng Huang, Francesco Ferretti, Helfried Neumann, Haijun Jiao, Robert Franke, Ralf Jackstell, Matthias Beller
Summary: By introducing 1,2-bis-di-tert-butylphosphin-oxylene (dtbpx) ligands, palladium-catalysed dicarbonylation of 1,3-butadiene can achieve high selectivity and efficiency, leading to a more cost-effective and environmentally friendly industrial production process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Inorganic & Nuclear
Francesco Ferretti, Luca Rota, Fabio Ragaini
Summary: The use of polymer-immobilized catalysts can enhance recovery efficiency but may also lead to reduced catalytic activity. By adjusting the structure of the polymer, a balance between catalytic activity and recovery efficiency can be achieved.
INORGANICA CHIMICA ACTA
(2021)
Article
Chemistry, Physical
Francesco Ferretti, Manar Ahmed Fouad, Fabio Ragaini
Summary: The reductive cyclization of β-nitrostyrenes using phenyl formate as a carbon monoxide surrogate in the presence of PdCl2(CH3CN)(2) + phenanthroline catalyst is a feasible method to synthesize indoles, achieving good yields when an aryl substituent is present in the starting nitrostyrene, but lower yields when no aryl substituent is present.
Article
Chemistry, Physical
Doaa R. Ramadan, Francesco Ferretti, Fabio Ragaini
Summary: This paper describes a palladium/phenanthroline catalyzed reductive cyclization of o-nitrobiphenyls to 9H-carbazoles operated by in situ released CO. The presence of phenyl formate is essential to avoid the use of high-pressure equipment and allows the reaction to be performed in a single thick-walled glass tube. The selectivity of the reaction is influenced by the identity of the base catalyzing the formate decomposition, and the stability of the catalyst is affected by the presence of chloride anions. The optimized catalytic system exhibits excellent stability and tolerance to moisture and air, enabling the reaction to be conducted with low catalyst loadings.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Analytical
Margherita Longoni, Francesco Ferretti, Sofia Zucca, Letizia Caielli, Silvia Bruni
Summary: In this study, surface-enhanced Raman spectroscopy (SERS) was used for the identification of dyes in chromogenic films. The results showed that SERS spectroscopy is an efficient technique for this purpose, and the excellent SERS properties of anisotropic nanomaterials were confirmed.
Article
Chemistry, Organic
Manar Ahmed Fouad, Francesco Ferretti, Fabio Ragaini
Summary: The reductive cyclization reaction of o-nitrostyrenes to generate indoles has been studied for three decades using CO as a cheap reducing agent. However, the use of toxic CO gas has limitations. In this study, formic acid was used as an effective reductant for reductive cyclization, providing high yields of indoles without generating toxic byproducts.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Editorial Material
Chemistry, Physical
Kotohiro Nomura, Raffaella Mancuso, Takeshi Ohkuma, Fabio Ragaini, Martin Kotora, Alfonso Grassi, Carl Redshaw, Armando Pombeiro, Ken-ichi Fujita, Carmine Capacchione, Kei Manabe, Victorio Cadierno
Article
Chemistry, Physical
Fabio Ragaini, Francesco Ferretti, Manar Ahmed Fouad
Summary: The reductive cyclization of organic nitro compounds catalyzed by transition metal complexes is an efficient and clean strategy for synthesizing N-heterocycles. However, it requires the use of autoclaves and pressurized CO lines. In this study, the authors used phenyl formate as a convenient CO surrogate, which liberated carbon monoxide under reaction conditions, allowing the use of a cheap glass pressure tube as a reaction vessel. The use of CO surrogates proved to be a viable alternative to gaseous reagents, with yields better than those reported using pressurized CO.
Article
Chemistry, Organic
Manar Ahmed Fouad, Francesco Ferretti, Simone Galie, Fabio Ragaini
Summary: In this study, formic acid was used as a surrogate for CO to successfully deoxygenate nitroarenes to nitrosoarenes, activated by acetic anhydride and a base. The nitrosoarenes were then trapped by conjugated dienes to form 3,6-dihydro-2H-[1,2]-oxazines. CuCl was employed as the catalyst to transform the oxazines into N-arylpyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Francesco Ferretti, Manar Ahmed Fouad, Cecilia Abbo, Fabio Ragaini
Summary: In this study, the formic acid/acetic anhydride mixture was utilized as a substitute for carbon dioxide (CO2) in the reductive cyclization reaction of o-nitrochalcones. By using a cheap and commercially available thick-walled glass tube without the need for any gaseous reagents, high yields comparable to those obtained with pressurized CO2 were achieved. The method was successfully applied to the three-step synthesis of the alkaloid Graveoline from commercially available and inexpensive reagents.