Article
Chemistry, Multidisciplinary
Jiaming Liu, Ming Chen
Summary: A Rhenium-catalyzed stereoselective transposition of allylic alcohols is described. In the presence of 1 mol% of Re2O7, (E)- or (Z)-δ-hydroxymethyl-anti-homoallylic alcohols were converted into the acetals of 2-methyl-1,3-syn-diols with excellent diastereoselectivities. 1,3-syn-Diol acetals can also be synthesized from (E)-δ-hydroxymethyl-syn-homoallylic alcohols.
Review
Chemistry, Organic
Sheng Zhang, Michael Findlater
Summary: This review focuses on cobalt-catalyzed alkene isomerization, including positional isomerization, geometric isomerization, and cycloisomerization. Three main types of reaction mechanism have been discussed to help the reader better understand and make meaningful comparisons.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Shelby M. Anderson, Marcus D. Van Engen, Paul E. Floreancig
Summary: The sequential allylic alcohol transposition, carbonyl group trapping, oxocarbenium ion formation, and nucleophilic addition result in ring formation and serve as a fragment-coupling and stereocenter-generating reaction. Balancing the kinetics of productive and unproductive steps is crucial for successful applications, and solvent changes can be used to expand the scope and change the stereochemical outcomes of the processes. Mechanistic studies provide insight into the transformations and reactive species generated.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
P. Rajesh, Abdulrahman Almansour, Natarajan Arumugam, Srinivasarao Yaragorla
Summary: A novel synthetic method utilizing an environmentally friendly catalyst has been developed for the efficient synthesis of 3-aminofurans, demonstrating high yields and broad substrate applicability. Preliminary photophysical studies have been conducted on the newly synthesized compounds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Ketan Kumar, Prashant Kumar, Bara Singh, Sonu Yadav, Uttam K. Mishra, Arshad J. Ansari, S. S. Ramasastry
Summary: The catalysis by transition metals is a powerful tool to access molecules with broad structural and functional diversity. Recent literature has shown the tremendous potential of transition metal-catalyzed processes in advancing organic synthesis. New conceptual advancements in palladium-catalyzed Alder-ene type cycloisomerization reactions, C-H functionalizations, and one-pot multicatalytic processes have become essential tools to access new classes of molecules.
Article
Chemistry, Multidisciplinary
Xufang Liu, Xianle Rong, Shihan Liu, Yu Lan, Qiang Liu
Summary: A novel method for the synthesis of chiral cyclic olefins, specifically 1-methylcyclohexenes, was reported in this study, enabling the construction of chiral compounds with diversified functionalities. The synthetic utility of this method was demonstrated by the concise and enantioselective synthesis of a natural product, beta-bisabolene, and further derivatizations showcased the versatility of the reaction products.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Chada Raji Reddy, Ketan Wadekar, Karna Nair, Y. Lakshmi Prapurna
Summary: A new approach for synthesizing benzofurans from non-aromatic precursors is reported. The method involves sequential DBU-mediated cycloisomerization for furanylation followed by benzene ring construction via oxidative aromatization. The reaction has advantages such as atom- and pot-economy, simple reaction conditions, easy preparation of starting materials, and access to diverse substituted benzofurans.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Applied
Jingyao Tan, Rui Wang, Li Xu, Wenli Wu, Meijia Deng, Wanhong Yuan, Li Li, Zhihua Lin
Summary: In this study, a general and efficient strategy for the synthesis of 2,3-disubstituted benzofurans using o-alkenyl phenols as starting materials was developed. The reaction cascade, catalyzed by HNTf2/TMSOTf, provided the desired products in moderate to good yields. This method offers the advantages of metal-free conditions, broad substrate scope, mild reaction conditions, and easy scalability.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
King Hung Nigel Tang, Kanako Uchida, Kazuki Nishihara, Mamoru Ito, Takanori Shibata
Summary: In this study, a catalytic reaction of N-benzylideneanilines with functionalized alkenes has been developed, leading to ortho-substituted benzaldehyde derivatives with a functional group at the remote position after acidic treatment. This transformation involves deconjugative long-range isomerization (chain-walking) up to 11 times and C-H activation using an imino group as a transient directing group.
Article
Chemistry, Physical
Miroslav Dangalov, Adolfo Fernandez-Figueiras, Martin A. Ravutsov, Ekaterina Vakarelska, Maya K. Marinova, Nuno R. Candeias, Svilen P. Simeonov
Summary: A Ru-catalyzed isomerization reaction of Achmatowicz derivatives is reported, providing unexplored routes for diversification of the biogenic furanic platform. Mechanistic insights were studied using computational and deuterium labeling techniques. This transformation proved to be a robust tool for the synthesis of bioderived monomers and 4-keto-o-valerolactones, enabling the flexible synthesis of acetogenins. Additionally, a concise and protective group-free asymmetric total synthesis of two natural products, (S,S)-muricatacin and (S,S)-L-factor, is described.
Article
Chemistry, Organic
Can Chen, Zhe Tian, Wanjie Liang, Jintao Guo, Ping Xiao, Zhenlei Wang, Lizhi Zhang, Qing Liu, Hui Liu
Summary: A ligand-free palladium-promoted [1,8]-sigmatropic hydrogen shift reaction of 1,6-allene-ene was reported, which involved an intramolecular Ene cyclization using base as a hydrogen shuttle. The transformation achieved hydrogen atom transfer (HAT) by shifting the allylic C-H bond to a new one with low bond dissociation energy (BDE) distinction. The mild reaction conditions, high atom economy, and good chemo/regioselectivity highlighted the significance of this strategy.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Ying Ding, Jinguo Long, Feilong Sun, Xianjie Fang
Summary: A nickel-catalyzed isomerization/allylic cyanation of alkenyl alcohols is reported, providing a new complement to allylic substitution reactions. The use of a specific diphosphite ligand and methanol as the solvent is crucial for the success of this transformation, as demonstrated by a gram-scale regioconvergent experiment and formal synthesis of quebrachamine showcasing the high potential of this methodology.
Article
Chemistry, Organic
Subhashini V. Subramaniam, Vijaya Kumaran Dharmalingam, Anwesha Bhattacharya, Saravanan Peruncheralathan
Summary: The first catalytic domino reaction of alpha-(2-formylaryloxy)acetonitriles with arylboronic acids has been disclosed, leading to a range of 2-aroylbenzo[b]furans. The reaction shows high yields, efficiency, and compatibility with various aryl boronic acids.
Article
Energy & Fuels
Lelia Cosimbescu, Kristen B. Campbell, Jotheeswari Kothandaraman, Deepika Malhotra, Marie S. Swita
Summary: This study demonstrates the formation of symmetrical and unsymmetrical allylic ethers using molybdenum catalysts for the first time. By optimizing reaction conditions, it was possible to maximize the conversion of prenol and generate the main products.
Article
Chemistry, Applied
Zhenli Liu, Guanghui Li, Tengfei Yao, Junliang Zhang, Lu Liu
Summary: A site-selective C(sp(2))-H functionalization of free phenols with 1,3-dienes was developed using Bronsted acid catalysis, particularly triflic acid, under mild conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
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, Organic
Lucia Veltri, Roberta Amuso, Tommaso Prestia, Paola Vitale, Bartolo Gabriele
Summary: In this study, a direct and multicomponent approach to synthesize important fused-ring heterocycles was reported. The reaction employs readily available building blocks and shows high yields of the desired products under mild conditions. The reaction proceeds through a sequence of ordered steps.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Andrea Macchia, Helene Aureli, Chiara Biribicchi, Antonella Docci, Chiara Alisi, Fernanda Prestileo, Francesco Galiano, Alberto Figoli, Raffaella Mancuso, Bartolo Gabriele, Mauro Francesco La Russa
Summary: Biodegradation is a common issue for Cultural Heritage stone materials outdoors. Traditional methods of biofilm removal are not effective in outdoor environments, thus the application of antimicrobial coatings is necessary. This study compared the effectiveness of innovative biocides and an antimicrobial coating on a Roman mosaic, and found promising results with the combination of biocide and the protective effect of the coating.
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.
