Article
Chemistry, Physical
Karla Almaraz, Manuel Amezquita-Valencia
Summary: A protocol for the synthesis of lactams fused to coumarins using a palladium-catalyzed hydroaminocarbonylation reaction was developed. The system showed good isolated yield and regioselectivity for seven-membered ring lactam synthesis. Control reactions demonstrated the importance of hydrogen in the reaction, and NMR data supported the role of a hydride palladium species as a catalyst precursor. Preliminary screening of the cytotoxic activity of these lactams against six cancer cell lines indicated the influence of heterocycle size and substituents on cell growth inhibition.
Article
Chemistry, Organic
Hideo Setsumasa, Kosuke Imai, Ikumi Kobayashi, Masahisa Nakada
Summary: The Pd-catalyzed stereoselective construction of decalins with one-carbon units bearing heteroatoms at the ring junction is described. The Pd-catalyzed cyclization of silyl enol ether resulted in exclusive formation of the cis isomer (89%, >100/1 cis/trans). On the contrary, Pd-catalyzed carboiodination and carboborylation (with oxidative workup) provided products in 56% yield (1/>100 cis/trans) and 69% yield (1/11 cis/trans), respectively.
Article
Chemistry, Organic
Hideo Setsumasa, Kosuke Imai, Ikumi Kobayashi, Masahisa Nakada
Summary: This study describes the Pd-catalyzed stereoselective synthesis of decalins with one-carbon units bearing heteroatoms at the ring junction. The Pd-catalyzed cyclization of silyl enol ether resulted in the exclusive formation of the cis isomer (89%, >100/1 cis/trans). Conversely, Pd-catalyzed carboiodination and carboborylation reactions (with oxidative workup) provided products with yields of 56% (1/>100 cis/trans) and 69% (1/11 cis/trans), respectively.
Article
Chemistry, Multidisciplinary
Chao Liu, Xiangwen Tan, Lingzhi Zhan, Yaru Jing, Wanqing Wu, Zhuofeng Ke, Huanfeng Jiang
Summary: A novel and efficient strategy for synthesizing fused benzo-aza-oxa-[5-6-5] tetracycles with high yields and diastereoselectivities has been demonstrated. This strategy involves the synthesis of functionally divergent anilines and 3-butenoic acid with five chemical bonds constructed. Control experiments and DFT calculations were performed to support the proposed mechanism.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jian-Shu Wang, Lingyun Yao, Jun Ying, Xiaoling Luo, Xiao-Feng Wu
Summary: A palladium-catalyzed regioselective cyclocarbonylation of N-(2-pyridyl)sulfonyl (N-SO2Py)-2-iodoanilines with allenes has been developed, achieving up to 95% yield of various 3-methylene-2,3-dihydroquinolin-4(1H)-ones. Control experiments and DFT calculations were conducted to understand the reaction details and propose a possible reaction mechanism.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Evgeny B. Ulyankin, Anastasia S. Kostyuchenko, Sergey A. Chernenko, Mikhail O. Bystrushkin, Anna L. Samsonenko, Anton L. Shatsauskas, Alexander S. Fisyuk
Summary: A new approach based on iodine-promoted photocyclization was developed for the synthesis of fused benzothiophene derivatives, providing an efficient method compared to traditional oxidative coupling and palladium-catalyzed intramolecular arylation. This method allows for the synthesis of a variety of functionally substituted fused heterocycles containing pyridine and carbazole moieties.
SYNTHESIS-STUTTGART
(2021)
Review
Chemistry, Multidisciplinary
Tapas Ghosh, Diptam Biswas, Sayantika Bhakta
Summary: The use of palladium catalysts in fused ring synthesis has gained increasing attention in recent years. Palladium catalysts have unique features that make them more widely applicable compared to other transition metal catalysts. Palladium plays an important role in various Heck reactions, producing diverse carbocycles and heterocycles of biological importance. In addition to intramolecular Heck-type reactions, several other reaction types have been extensively employed to access fused carbo- and heterocycles. This review article provides a comprehensive overview of the applications and mechanisms of using palladium catalysts in fused ring synthesis since 2001.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Sawsan H. Alelaiwi, James R. Mckee
Summary: A direct and effective method for synthesizing primary amine of several polycyclic aromatic compounds through copper (I)-catalyzed Ullmann C-N coupling is reported. This method also allows the synthesis of new N-substituted dibenzothiophene derivatives. The use of inexpensive catalysts and aqueous ammonia as the ammonia source makes this protocol environmentally and economically advantageous.
Article
Chemistry, Organic
Pengcheng Xu, Bo Qian, Zaojuan Qi, Bao Gao, Bin Hu, Hanmin Huang
Summary: A method for synthesizing quinolizinone with potential bioactivity has been developed through palladium-catalytic dearomative cyclocarbonylation of allyl alcohol, resulting in efficient production of diverse quinolizinone compounds. The feasible reaction pathway likely involves allylation, dearomatization, CO insertion, and the Heck reaction in a successive procedure.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Changtong Zhu, Zhenbo Yuan, Zhiwei Deng, Dejing Yin, Yan Zhang, Jingwen Zhou, Yijian Rao
Summary: By engineering the enzyme GluER and combining it with photoenzymatic synthesis, the efficient asymmetric synthesis of oxygen-containing benzo-fused heterocycles has been achieved, providing a green approach for the synthesis of important chiral motifs in pharmaceuticals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Inorganic & Nuclear
Jun Gu, Fengyue Zhao, K. N. Houk, Qianqian Lu, Fang Liu
Summary: The palladium-catalyzed annulation of o-haloanilines with CO and CO2 for the synthesis of isatoic anhydrides was studied using DFT calculations. The results show that carbonylation precedes carboxylation in the mechanism, and the base plays a crucial role in facilitating the reaction. The study demonstrates the perfect cooperation of CO and CO2 in constructing an anhydride moiety for o-haloanilines.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Multidisciplinary
Yan Zheng, Mengke Dong, Erdong Qu, Jin Bai, Xiao-Feng Wu, Wanfang Li
Summary: A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives was developed by Pd-catalyzed carbonylative cross-coupling, which does not require toxic and flammable CO gas and tolerates a wide scope of functional groups. Remarkably, this method can be used to construct natural products and drugs containing 4H-benzo[d][1,3]oxazin-4-one structures.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Applied
Xiao Yang, Rui Sun
Summary: Transition-metal-catalyzed oxidative annulation reactions are efficient methods for the synthesis of benzo-fused heterocyclic compounds. This review focuses on recent developments in reaction conditions and coupling reagents, aiming to provide sustainable and versatile strategies for the construction of heterocyclic skeletons found in drugs and bioactive molecules. The review summarizes and categorizes the annulation mechanisms with different coupling reagents.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Christian H. Schiwek, Simone Stegbauer, Thomas Pickl, Thorsten Bach
Summary: In this study, a diastereoselective arene hydrogenation reaction was reported and applied to benzo-fused N-heterocycles. A total of 48 saturated heterocycles were obtained by hydrogenation with yields of 72-98% and moderate to high diastereoselectivities.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Lijun Shi, Mingshan Wen, Fuwei Li
Summary: The study reports a selective method for the synthesis of fused N-heterocycles through palladium-catalyzed tandem reactions, which successfully addresses the selectivity issue in the presence of incompatible step reactions and effectively prevents side reactions.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Martina Capua, Serena Perrone, Filippo Maria Perna, Paola Vitale, Luigino Troisi, Antonio Salomone, Vito Capriati
Article
Chemistry, Organic
Martina Capua, Serena Perrone, Fabio Bona, Antonio Salomone, Luigino Troisi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Serena Perrone, Martina Capua, Francesco Messa, Antonio Salomone, Luigino Troisi
Article
Chemistry, Multidisciplinary
Francesco Messa, Serena Perrone, Martina Capua, Francesco Tolomeo, Luigino Troisi, Vito Capriati, Antonio Salomone
CHEMICAL COMMUNICATIONS
(2018)
Review
Chemistry, Organic
Serena Perrone, Luigino Troisi, Antonio Salomone
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Andrea Nicola Paparella, Francesco Messa, Giuseppe Dilauro, Luigino Troisi, Serena Perrone, Antonio Salomone
Summary: A glycerol-based Deep Eutectic Solvent (DES) has been developed as a recyclable and efficient catalyst system for the Pd-catalyzed activation of (hetero)arylchlorides and the formation of 2,2'-bipiyridines and biaryls. The use of DES eliminates the need for external reducing agents as glycerol acts as a safe and green organic reductant. This catalyst system has been successfully applied to the sustainable synthesis of the Abametapir drug.
Article
Engineering, Environmental
Francesca Lionetto, Carola Esposito Corcione, Francesco Messa, Serena Perrone, Antonio Salomone, Alfonso Maffezzoli
Summary: This study investigates the challenges associated with adsorption studies of contaminants on microplastics (MPs) in the marine environment and explores the adsorption of amoxicillin on different types of MPs. The results show that aged MPs absorb a higher antibiotic content than unaged ones due to their different specific surface areas. The thermodynamic affinity between amoxicillin and PET MPs is analyzed through Hansen's solubility parameters, and a potential interaction mechanism based on hydrogen bonding is hypothesized. Additionally, it is found that PET MPs can serve as carriers for pollutant transport in the aquatic environment.
JOURNAL OF POLYMERS AND THE ENVIRONMENT
(2023)
Article
Chemistry, Multidisciplinary
Maria J. Rodriguez-Alvarez, Sergio E. Garcia-Garrido, Serena Perrone, Joaquin Garcia-Alvarez, Vito Capriati
Summary: The use of Deep Eutectic Solvents (DESs) as reaction media for transition-metal-catalyzed organic transformations has gained significant interest in the past decade. These solvents, derived from renewable and non-toxic precursors, offer advantages such as easy recyclability and compatibility with heterogeneous catalysis. Recent studies have demonstrated the efficient coupling of transition-metal-based nanoparticles with DESs in various synthetic protocols, including coupling reactions, oxidation/reduction processes, heterocycle synthesis, and polymerization reactions.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2023)
Article
Chemistry, Organic
Francesco Messa, Andrea Nicola Paparella, Dominik Vesely, Jozef Krajcovic, Paride Papadia, Serena Perrone, Antonio Salomone
Summary: The Pd-catalyzed amino- and alkoxycarbonylation of aryl iodides has been successfully carried out in a bioinspired Deep Eutectic Solvent and under gas-free conditions using Mo(CO)(6) as the CO source. This method provides a high-yielding (up to 99%) and efficient synthesis of carboxylic amides and esters in a short reaction time (2 h) and under mild reaction conditions (80 degrees C) with a low catalyst loading (2.5 mol %).
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Serena Perrone, Francesco Messa, Antonio Salomone
Summary: Hydrogenation processes, which add two hydrogen atoms to unsaturated bonds, are widely used in the manufacture of bulk and fine chemicals. However, these reactions have typically been carried out in volatile and often toxic organic solvents derived from petroleum. This review describes recent advances in reducing methodologies that aim to use sustainable and benign solvents derived from renewable sources, without sacrificing process efficiency and selectivity. Important aspects of green chemistry, such as catalyst recovery and product isolation, have been considered in the choice of these methodologies.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Francesco Messa, Serena Perrone, Antonio Salomone
Summary: A novel uracil derivative, 3-cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione (4), was synthesized via a four-component reaction involving an α-chloroketone (1), an aliphatic isocyanate (2), a primary aromatic amine (3) and carbon monoxide. The reaction mechanism involved Pd-catalyzed carbonylation and in situ formation of non-symmetrical urea, leading to the formation of 3-cyclohexyl-6-phenyl-1-(p-tolyl)pyrimidine-2,4(1H,3H)-dione (4). The uracil derivative 4 was isolated in good yield (73%) and fully characterized by various spectroscopic techniques.
Article
Chemistry, Organic
Francesco Messa, Andrea Nicola Paparella, Serena Perrone, Antonio Salomone
Summary: For the first time, Pd-catalyzed alkoxycarbonylation of aryl iodides has been investigated in phosphonium-based deep eutectic solvents under gas-free conditions using Mo(CO)(6) as the CO source. This method allows the efficient synthesis of ethylene glycol and glycerol esters with high yields (up to 99%), short reaction times, and mild reaction conditions, utilizing a remarkably low catalyst loading (0.5 mol%).
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Andrea Nicola Paparella, Francesco Messa, Serena Perrone, Antonio Salomone
Summary: Treatment of internal alkynes with Al powder, Pd/C, and basic water in a methyltriphenylphosphonium bromide/ethylene glycol eutectic mixture yields highly chemoselective formation of (Z)-alkenes, with yields up to 99% and Z/E stereoselectivity ranging from 63/37 to 99/1. The unusual catalytic activity of Pd/C is believed to be modulated by the in situ formation of a phosphine ligand.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Francesco Messa, Giuseppe Dilauro, Andrea Nicola Paparella, Lavinia Silvestri, Guido Furlotti, Tommaso Iacoangeli, Serena Perrone, Antonio Salomone
Summary: This article presents a novel reductive protocol for the reduction of organic compounds under Pd-catalysis, using aluminum and water to in situ generate H-2 in deep eutectic solvents. The method demonstrates both generality and safety, and exhibits excellent scalability in the synthesis of active pharmaceutical ingredients.
Article
Chemistry, Multidisciplinary
Giuseppe Dilauro, Francesco Messa, Fabio Bona, Serena Perrone, Antonio Salomone
Summary: A simple cobalt complex, Co(phen)Cl₂, has been found to be a highly efficient and cost-effective precatalyst for various cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl, and alkyl bromides. New C(sp²)-C(sp²) and C(sp²)-C(sp³) bonds can be formed in good to excellent yields and high chemoselectivity under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
