Article
Chemistry, Organic
Gaurav Badhani, Abhisek Joshi, Subbarayappa Adimurthy
Summary: The study introduces a metal-free method for the synthesis of imines using oxygen as the terminal oxidant, achieving oxidative coupling of amines and alcohols to form C-N, C-S, and C-C bonds. This method features mild reaction conditions and broad applicability.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Letter
Chemistry, Organic
Shaocheng Li, Thayalan Rajeshkumar, Jincheng Liu, Laurent Maron, Xigeng Zhou
Summary: Here, we describe a redox-neutral rare earth catalyst that enables the first catalytic decarbonylation and decarbonylative hydroamination of formamides without using additives. The protocol exhibits complete N-aryl/alkenyl formamide-selectivity, thus offering a diverse range of possibilities for N-formylation and N-deformylation methods, and opening up new prospects for waste reduction and control of selectivity in amine transformation events.
Article
Chemistry, Organic
Fanni Bede, Laszlo Kollar, Nandor Lambert, Peter Huszthy, Peter Pongracz
Summary: Palladium-catalyzed hydroaminocarbonylation reactions of olefins using aliphatic amines were successfully performed under carbon monoxide atmosphere. The targeted amides were synthesized in moderate to good isolated yields without the need for acidic additives. The effect of chiral diphosphines on product distribution, including chemo-, regio-, and enantioselectivities, was also investigated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Khushboo Verma, Ashutosh Sharma, Jasminder Singh, Rahul Badru
Summary: In this work, a series of DBU-based monocationic and dicationic ionic liquids with various anions were synthesized, characterized, and utilized as catalysts in the carbamation of amines with dimethyl carbonate. A detailed study was conducted to probe the mechanistic establishment of the carbamation process, elucidating the role of DBU and DBU-derived ionic liquids as catalysts. The attachment of a butyl group to the nitrogen of the DBU unit reversed the selectivity, as confirmed by spectral techniques and theoretical studies (DFT). The best carbamate yields were obtained using [BuDBU]Ala IL under optimized reaction conditions, and this IL catalyst could be efficiently reused five times without significant catalytic loss.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2023)
Article
Chemistry, Multidisciplinary
Khushboo Verma, Ashutosh Sharma, Jasminder Singh, Rahul Badru
Summary: The study demonstrated the selective synthesis of carbamates from amines using imidazolium-based ionic liquids as catalysts and dimethylcarbonate as the carbonylating agent. The ionic liquids showed excellent catalytic activity and could be easily recovered and reused, making the protocol simple, cost-effective, solvent-free, and sustainable.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2021)
Article
Chemistry, Organic
Yan-Hua Zhao, Xing-Wei Gu, Xiao-Feng Wu
Summary: This paper reports a ligand-free visible-light-induced manganese-catalyzed carbonylation reaction for the synthesis of various amides. The method offers advantages such as low cost and low toxicity, and can proceed effectively at ambient temperature and pressure.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Physical
Kai-Lun Bi, Bao-Hua Xu, Wei-Lu Ding, Li-Jun Han, Lin Ji
Summary: The Ru-catalyzed carbonylation of alkenes using CO2 and imidazole chlorides as the promotor was studied through computational and experimental analysis. The efficiency of hydroesterification and hydroformylation was found to be correlated with the conversion rate of CO2 to CO, which was facilitated by chloride additives, particularly BmimCl and B3MimCl > BmmimCl > LiCl. In the hydroesterification reaction with MeOH, BmimCl with C-H functionality at the C2 site of the cation acted as a hydrogen donor medium, with the anion and cation working synergistically. The insertion of CO2 into the formed Ru-H bond with the assistance of chloride anion produced the Ru-COOH species, accelerating the activation of CO2.
GREEN ENERGY & ENVIRONMENT
(2023)
Article
Chemistry, Inorganic & Nuclear
Yiwen Zhu, Zhengjie Le, Jun Ying, Xiao-Feng Wu
Summary: A palladium-catalyzed double carbonylation reaction has been developed for the rapid construction of 4-oxo-4-(aryl/alkylamino)butanoic acid scaffolds, using benzene-1,3,5-triyl triformate (TFBen) as the CO surrogate. The reaction with aromatic and aliphatic primary amines proceeded well, yielding a variety of functionalized acids in high yields.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Barbara Hanna Roman, Magdalena Chareza, Ewa Janus, Radoslaw Drozd
Summary: Twenty new triethanolammonium amino acid salts (TEA AA) were synthesized and their physicochemical properties were investigated. These salts showed a range of melting points and glass transition temperatures, indicating their suitability as amino acid ionic liquids (AAILs). The TEA AA salts were tested as additives for proteolytic enzymes, showing inhibitory effects with different mechanisms depending on the enzyme and salt used. The results suggest that these TEA AA salts have potential as enzyme-controlling agents in industrial processes.
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
(2023)
Article
Biochemistry & Molecular Biology
Ting He, Cheng-Bin Hong, Peng-Chong Jiao, Heng Xiang, Yan Zhang, Hua-Qiang Cai, Shuang-Long Wang, Guo-Hong Tao
Summary: The study systematically examined the Bronsted acidity of [AAE]X PILs in green solvents and found that the cationic structures had little effect on the acidity, while the anions had no effect. Four different methods were used to determine the acidic strength, including the overlapping indicator method, potential titration method, Hammett method, and DFT method. These methods were reliable for assessing the acidity of [AAE]X.
Article
Chemistry, Physical
Le-Cheng Wang, Xiao-Feng Wu
Summary: In this study, we have developed an unprecedented and general method for the direct synthesis of various alpha-amino acid derivatives by activating inert C-H bonds. By introducing an appropriate electron-withdrawing group, we successfully modulated the nucleophilicity and polarity of the reaction, resulting in a broad substrate scope and excellent tolerance of sensitive functional groups in this catalytic strategy.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jorge Cardenas, Ruben Gavino, Erendira Garcia-Rios, Lucero Rios-Ruiz, Ana C. Puello-Cruz, Francisco Neptali Morales-Serna, Samuel Gomez, Adolfo Lopez-Torres, Jose Antonio Morales-Serna
Summary: The palladium-catalysed reaction of aryl halides and allylic alcohols is an important method for obtaining alpha, beta-unsaturated aldehydes and ketones. A 1,2,3-triazol-5-ylidene (aNHC)-based palladium(ii) complex formed in situ has been found to be a selective catalyst with yields ranging from 50% to 90%. The lack of toxic effects of the ligand precursor on the harpacticoid copepod Amphiascoides atopus allows for a comparison of catalytic efficiency with the potential impact of waste chemicals on global aquatic ecosystems.
Article
Chemistry, Multidisciplinary
Minghui Zhu, Qinglong Zhang, Weiwei Zi
Summary: The study presents a dual-metal catalyzed diastereodivergent coupling method for the synthesis of beta-amino alcohols with multiple stereoisomers, enabling the concise preparation of natural products such as mycestericins F and G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Hui Deng, Chali Liu, Xin Xu, Yuanyuan Wu, Muhan Chen, Zhangjie Huang
Summary: In this study, three imidazolium-based ionic liquids were synthesized and used to construct microemulsion systems for the recovery of Pd (II) from cyanide media. The [BUIm]Br/n-heptane/n-pentanol/sodium chloride microemulsion system exhibited the highest extraction percentage. After optimization, the extraction percentages of Pd (II) using the [BUIm]Br/n-heptane/n-pentanol/sodium chloride microemulsion system were all above 98.5%. The proposed process has the potential for comprehensive treatment of cyanide metallurgical wastewater.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Laura Cocheci, Lavinia Lupa, Nick Samuel Tolea, Radu Lazau, Rodica Pode
Summary: This study successfully synthesized and functionalized Mg3Al-LDH to obtain efficient adsorbent materials for palladium removal from aqueous solutions.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Applied
Aleksandr Voronov, Alessandra Casnati, Paolo P. Mazzeo, Paolo Pelagatti, Alessia Bacchi, Raffaella Mancuso, Bartolo Gabriele, Elena Motti, Giovanni Maestri, Peter Pal Feher, Andras Stirling, Nicola Della Ca'
Summary: A new method for the transformation of propargyl ureas to 2-aminooxazolines using Ag(I) catalysis is disclosed in this article, providing good yields and complete stereoselectivity. A one-pot protocol starting from propargylic amines and isocyanates has also been developed. Insights into the tautomeric equilibrium and relative reactivity of 2-aminooxazoles are provided.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Vinayak Botla, Marco Fontana, Aleksandr Voronov, Raimondo Maggi, Elena Motti, Giovanni Maestri, Nicola Della Ca'
Summary: Despite the advances in carbon-halogen bond formation, the selective functionalization of iodoaryls is still challenging. In this study, a one-pot synthesis of ortho-iodobiaryls from aryl iodides and bromides is reported using palladium/norbornene catalysis. The Catellani reaction involves the cleavage of a C(sp(2))-I bond, ortho C-H activation, oxidative addition of an aryl bromide, and restoration of the C(sp(2))-I bond, leading to the formation of palladacycles. A variety of valuable o-iodobiaryls have been synthesized with good yields, and their derivatization is described. A DFT study provides insights into the mechanism of the key reductive elimination step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Environmental Sciences
Vu T. Luong, Edgardo E. Canas Kurz, Ulrich Hellriegel, Duc N. Dinh, Hang T. Tran, Alberto Figoli, Bartolo Gabriele, Tran L. Luu, Jan Hoinkis
Summary: This study developed and tested a modular desalination system combining membrane capacitive deionization (MCDI) with low-pressure reverse osmosis (LPRO). The system was evaluated and compared with conventional seawater reverse osmosis (SWRO) at different salinities. The pilot tests conducted in the Can Gio region of South Vietnam showed that the system achieved drinking water quality with low energy consumption. The study also investigated fouling mitigation methods for the ultrafiltration pre-treatment.
JOURNAL OF ENVIRONMENTAL MANAGEMENT
(2023)
Review
Chemistry, Physical
Bartolo Gabriele, Raffaella Mancuso, Nicola Della Ca, Lucia Veltri, Ida Ziccarelli
Summary: This article provides an overview of catalytic carbonylative double cyclization reactions, where organic substrates and carbon monoxide are sequentially activated to form two new cycles with the incorporation of carbon monoxide. It highlights the power of this synthetic methodology in the one-step synthesis of complex molecular architectures using readily available CO as the building block. The review is divided into five sections: Introduction, Functionalized Olefinic Substrates, Functionalized Acetylenic Substrates, Functionalized Halides, and Conclusions and Future Perspectives.
Review
Chemistry, Multidisciplinary
Bartolo Gabriele, Nicola Della Ca', Raffaella Mancuso, Lucia Veltri, Ida Ziccarelli
Summary: This microreview provides an overview of the recent advances (2020 to September, 2022) in synthetic methods using amidine and guanidine for carbon dioxide capture and utilization. The use of these superbases has shown to facilitate CO2 capture and the formation of stable carbamate salts. Furthermore, these superbases have also enabled the incorporation of CO2 into functionalized organic substrates.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2023)
Article
Chemistry, Organic
Diego Olivieri, Riccardo Tarroni, Carla Carfagna
Summary: The synthesis of dibenzyl-(1S*,2S*)-2,3-dihydro-1H-indene-1,2-dicarboxylate is achieved by a diastereospecific bis-alkoxycarbonylation reaction using 1H-indene, benzyl alcohol, and carbon monoxide. The catalyst is formed in situ by mixing Pd(TFA)(2), the ligand N-2,N-3-bis(2,6-dimethylphenyl)butane-2,3-diimine, and p-benzoquinone as the oxidant.
Article
Chemistry, Multidisciplinary
Raffaella Mancuso, Alex De Salvo, Patrizio Russo, Aurelia Falcicchio, Nicola Della Ca, Leonardo Pantoja Munoz, Bartolo Gabriele
Summary: The PdI2/KI-catalyzed oxidative carbonylation of 4-(2-aminophenyl)-3-yn-1-ols selectively produces dihydrofuroquinolinone derivatives in fair to high yields (60%-89%) and excellent turnover numbers (180-267 mol of product per mol of Pd) over 19 examples. This reaction involves the catalytic construction of two rings and three new bonds in one step, providing high value added fused heterocyclic structures from readily available materials.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Physical
Mario Prejano, Raffaella Mancuso, Tiziana Marino, Bartolo Gabriele
Summary: In this study, a detailed computational investigation was conducted on the conversion of 1-(methylthio)-3-yn-2-ols to thiophene-3-carboxylate esters using PdI2/KI catalyst. The study provides insights into the role of each species involved in the reaction mechanism and confirms the experimental data.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Chiara Biribicchi, Andrea Macchia, Gabriele Favero, Romina Strangis, Bartolo Gabriele, Raffaella Mancuso, Mauro Francesco La Russa
Summary: This study investigates the use of hydrophobic Deep Eutectic Solvents (DESs) as alternatives to toxic solvents for removing nonpolar coatings from works of art. Beeswax and two microcrystalline waxes were tested, and the interaction between DESs and the waxes was evaluated using various tests. The results show that DESs have the potential to be used as green solvents for cleaning Cultural Heritage.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Ida Ziccarelli, Lucia Veltri, Tommaso Prestia, Roberta Amuso, Maria A. Chiacchio, Raffaella Mancuso, Bartolo Gabriele
Summary: Unreported 2-(4-acylfuran-2-yl)acetamides were selectively synthesized in fair to good yields (54-81%) over 19 examples through a mild catalytic process involving Csp-H activation, 5-exo-dig O-cyclization, and aromative isomerization.
