Article
Chemistry, Organic
Stephane Golling, Pierre Hansjacob, Nassim Bami, Frederic R. Leroux, Morgan Donnard
Summary: This paper reports a palladium-catalyzed annulation reaction that can synthesize polysubstituted amino-indenones, with different regioselectivity observed between different ynamides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zijun Huang, Yudong Li, Jiaxing Zhou, Yi Zhang, Jiacheng Wu, Yongkai Wu, Fan Zhang, Zhengjun Fang, Yuehui Li
Summary: In this study, a palladium-catalyzed carbonylation reaction using CO2 and waste hydrosilane PMHS was developed for the synthesis of aurones from terminal aromatic alkynes and 2-iodophenols. Various terminal alkynes and substituted 2-iodophenols were efficiently converted to the corresponding aurones. The mechanistic investigation suggests that the silyl formate derived from CO2 and PMHS plays a crucial role in the carbonylation reaction.
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.
Article
Chemistry, Physical
Xing Ge, Xiuyu Fang, Ren-Guan Miao, Xinxin Qi, Xiao-Feng Wu
Summary: A general and efficient protocol has been developed for the synthesis of acetamide-functionalized benzofurans using a palladium-catalyzed intramolecular cyclization and reductive aminocarbonylation reaction. The reaction proceeds in a single step, resulting in structure-defined benzofurans with acetamides as attractive functional groups. Various acetamide-functionalized benzofurans were obtained with moderate to good yields and good functional group compatibility using Mo(CO)6 as both CO source and reductant.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Raffaella Mancuso, Romina Strangis, Ida Ziccarelli, Nicola Della Ca, Bartolo Gabriele
Summary: The study reports the first example of a palladium-catalyzed oxidative carbonylative S-cyclization process conducted under aerobic conditions, leading to the successful synthesis of thiophene-3-carboxylic esters in one step. By utilizing specific substrates and reaction conditions, the transformation was achieved efficiently.
JOURNAL OF CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Xiaolei Ji, Chaoren Shen, Xinxin Tian, Hongru Zhang, Xinyi Ren, Kaiwu Dong
Summary: In this study, a Pd-catalyzed asymmetric double hydroxycarbonylation of terminal alkynes was developed using relay catalysis, which provided an efficient route to chiral succinic acids. This method demonstrated high yields and enantioselectivity for 41 examples and showcased its synthetic utilities in the facile synthesis of key intermediates for chiral pharmaceuticals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Raffaella Mancuso, Patrizio Russo, Melania Lettieri, Domenico Santandrea, Corrado Cuocci, Bartolo Gabriele
Summary: Polycyclic heterocyclic derivatives can be synthesized in one step by a carbonylative double cyclization approach, with yields ranging from 45% to 86%, showing promising potential for various applications.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Ida Ziccarelli, Raffaella Mancuso, Francesco Giacalone, Carla Calabrese, Valeria La Parola, Alex De Salvo, Nicola Della Ca', Michelangelo Gruttadauria, Bartolo Gabriele
Summary: This article reports the successful heterogenization of the classical PdI(4)(2-)carbonylation catalyst on multi-walled carbon nanotubes. The newly developed heterogeneous catalyst shows good activity and recyclability in the oxidative monoaminocarbonylation reaction, with limited metal contamination in the final organic compounds.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Caijin Zeng, Shaoting Su, Songjia Fang, Huangfeng Jiang, Shaorong Yang, Wanqing Wu
Summary: A novel palladium-catalyzed three-component carbonylation reaction has been developed for the efficient assembly of 1,3-substituted maleimides from haloalkynes and simple anilines. The reaction exhibits high chemo- and regioselectivities, and operates under mild conditions.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Physical
Jian-Shu Wang, Jiangjie Zhang, Siqi Wang, Jun Ying, Chuan-Ying Li, Xiao-Feng Wu
Summary: A novel palladium-catalyzed domino carbonylative cyclization has been developed for the rapid construction of functionalized heterocycles. The reaction proceeds smoothly with the consecutive formation of C-C and C-X bonds using benzene-1,3,5-triyl triformate as the CO source, yielding a variety of biologically relevant derivatives.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Physical
Dan Wen, Xing Ge, Ren-Guan Miao, Xinxin Qi, Xiao-Feng Wu
Summary: A palladium-catalyzed carbonylative synthesis of carboxamide substituted 2-pynones from methyl enynoates and nitroarenes has been developed. A wide range of carboxamide substituted 2-pynones were obtained in moderate to high yields with quite high functional group compatibility using nitroarenes as the nitrogen sources and Mo(CO)6 as both CO surrogate and reductant. Late-stage modifications of natural molecules were also achieved.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Applied
Raffaella Mancuso, Melania Lettieri, Ida Ziccarelli, Patrizio Russo, Antonio Palumbo Piccionello, Bartolo Gabriele
Summary: A catalytic carbonylative approach is presented for the multicomponent synthesis of benzothiophene derivatives, based on an S-cyclization-demethylation-alkoxycarbonylation-reduction sequence promoted by the PdI2/KI catalytic system under relatively mild conditions. Benzothiophene-2-acetic esters are obtained in moderate to good yields starting from variously substituted substrates in combination with different alcohols as external nucleophiles.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Yong He, Hao Wang, Yao Zhou, Kai Yang, Qiuling Song
Summary: We report the highly regioselective synthesis of 5- and 4-(2,1-azaborine) substituted isoxazoles via [3 + 2] cycloaddition reactions between nitrile oxides and B-ethynyl-1,2-azaborines. 5-(2,1-azaborine) substituted isoxazoles are favored in the absence of a catalyst, while 4-(2,1-azaborine) substituted isoxazoles are favored in the presence of a ruthenium catalyst. The reaction exhibits excellent regioselectivity, mild reaction conditions, high functional group tolerance and a broad substrate scope.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Physical
Jiangjie Zhang, Jun Ying, Xiao-Feng Wu
Summary: A novel palladium-catalyzed tandem cyclization and carbonylation reaction was developed for the synthesis of indeno[1,2-b]indol-10(5H)-one derivatives. The reaction proceeded smoothly with high yields using formic acid as the CO source. This method can also be applied for the modification of various bioactive molecules.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Yuanrui Wang, Xiao-Feng Wu
Summary: A palladium-catalyzed redox-neutral dicarbonylation of terminal alkynes has been developed, using hydroxylamine as both a nucleophile and a potential oxidant. Maleimides were synthesized in moderate yields under relatively mild conditions without the addition of equivalent oxidants. This reaction involves Pd-H addition to the alkyne and the role of hydroxylamine ester intermediate as an internal oxidant via nucleophilic attack.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Physical
Andrea Macchia, Romina Strangis, Sara De Angelis, Marica Cersosimo, Antonella Docci, Michela Ricca, Bartolo Gabriele, Raffaella Mancuso, Mauro Francesco La Russa
Summary: Biodeterioration is a common degradation process in cultural heritage conservation, and chemical treatments can be harmful to the environment and operators. Deep eutectic solvents (DESs) are an eco-friendly alternative that can be used to treat biologically deteriorated stone surfaces. This study tests five different DESs and the preliminary results show promising potential for their application in the field of cultural heritage.
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
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, 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.
