Article
Chemistry, Organic
Taiga Yurino, Sunaho Saito, Mizuki Ichihashi, Takeshi Ohkuma
Summary: A Pd(OAc)(2)/P(OPh)(3) combination catalyst was used for the Tsuji-Trost-type allylic amination under aerobic conditions, and it was found that the reaction proceeded efficiently only when allylic phosphates were employed as electrophiles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Junxia Yang, Yan Zhang, Ruyu Zhu, Ying Xue
Summary: The density functional theory investigations elucidated the mechanism and origin of regioselectivity for the Pd(OAc)(2)-catalyzed reaction, revealing the most favorable reaction pathway and the origin of selectivity through computational analysis.
JOURNAL OF PHYSICAL CHEMISTRY A
(2021)
Article
Chemistry, Organic
Qingkun Wu, Jingxuan Hou, Qingshan Gu, Hui Gao, Meiqi Shi, Lu Zheng
Summary: A PhI(OAc)(2)/Pd(OAc)(2) system has been developed that synergistically promotes the formation of 8-hydroxyquinoline derivatives from benzoxazoles and alcohols. The reaction proceeds smoothly with a variety of benzoxazoles and alcohols, giving moderate yields of the corresponding 8-hydroxyquinoline derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Applied
Bingxiang Xue, Jie Shen, Sourav Manna, Angelino Doppiu, Lukas J. Goossen
Summary: A new catalyst has been discovered that can selectively introduce a primary amino group into aromatic compounds, and it can efficiently promote the amination reaction to synthesize primary anilines within 30 minutes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Rayavarapu Padmavathi, Srinivasarao Arulananda Babu
Summary: This paper reports a Pd(ii)-catalyzed bidentate directing group 8-aminoquinoline-aided, site-selective beta-C-H functionalization protocol for assembling modified azobenzene carboxamides, which enriches the library of modified azobenzene motifs. Considering the importance of azobenzenes in chemical sciences, this work provides a new route for their enrichment.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Shuai Yang, Yanghui Zhang
Summary: Alkene-relayed C-H activation is a promising strategy for selective functionalization of C-H bonds. We have developed a Pd-catalyzed annulation reaction of 2-iodobiphenyls with maleimides as a relay for C-H alkylation. This reaction demonstrates broad substrate scope and high efficiency, providing a straightforward method for the synthesis of succinimide-fused 9,10-dihydrophenanthrenes. Additionally, a reaction utilizing acenaphthylene as the relay has been developed, enabling easy access to dibenzo[j,l]fluoranthenes.
Article
Chemistry, Organic
Shuai Yang, Yanghui Zhang
Summary: Alkene-relayed C-H activation is a novel strategy for selectively functionalizing C-H bonds. In this study, we developed a Pd-catalyzed annulation reaction using 2-iodobiphenyls and maleimides as a relay for C-H alkylation. The reaction exhibited a broad substrate scope and high efficiency, providing a straightforward method for synthesizing succinimide-fused 9,10-dihydrophenanthrenes. Additionally, we also developed a reaction using acenaphthylene as the relay, allowing easy access to dibenzo[j,l]fluoranthenes.
Article
Chemistry, Inorganic & Nuclear
Rui Wang, Yangqiu Liu, Qianyue Wang, Lin Zhang, Zhewei Li, Min Pu, Ming Lei
Summary: In this study, the mechanism of C-O bond activation of butanoic acid substrates with the 8-aminoquinoline (AQ) group catalyzed by Pd(OAc)(2) was investigated using density functional theory. The results revealed that the protodepalladation step is the rate-determining step. The presence of AQ directing group is critical for regioselectivity in C-H activation and beta-O elimination steps.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Rahul K. Shukla, Akshay M. Nair, Chandra M. R. Volla
Summary: Recent years have witnessed the development of transition metal catalyzed C-H activation as a powerful method in organic synthesis. Allene reactivity has attracted considerable interest among synthetic chemists. Although directing group assisted C(sp(2))-H functionalization with allenes has been well studied, coupling with more challenging aliphatic C(sp(3))-H bonds remains a challenge. Here, we report a Pd(ii) catalyzed aliphatic C(sp(3))-H dienylation using allenyl acetates directed by 8-aminoquinoline. A wide range of carboxylic acids, including fatty acids and amino acids, were effectively functionalized at the beta and gamma positions to provide diversely functionalized 1,3-dienes. Preliminary mechanistic studies suggest that the success of this transformation relies on the crucial role of the base. The reaction proceeds through regioselective 2,3-migratory insertion of the allene with the alkylpalladium(ii) species followed by beta-acetoxy elimination.
Article
Chemistry, Multidisciplinary
Sylvain Bertho, Radhouan Maazaoui, Damla Torun, Ismael Dondasse, Raoudha Abderrahim, Cyril Nicolas, Isabelle Gillaizeau
Summary: An attractive and cost-effective alternative approach using FeCl2 or non-toxic iron powder was developed for the beta-C(sp(2))-H (fluoro)alkylation of a range of cyclic and acyclic non-aromatic enamides, showing regioselectivity, broad substrate scope, and good functional group tolerance.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wang Miao, Jinyu Zhang, Yanyan Yang, Weijun Tang, Dong Xue, Jianliang Xiao, Huaming Sun, Chao Wang
Summary: The transformation of alcohols into value-added products is of great importance, and this study achieved the selective functionalization of a sp(3) C-H bond on the alkyl side chain of an alcohol, expanding the chemical space of alcohols using the borrowing hydrogen strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Letter
Chemistry, Organic
Jianjun Wang, Daguo Hu, Xiaofeng Sun, Huiying Hong, Yian Shi
Summary: This work presents an efficient Pd-catalyzed ortho-C-H amination reaction of N-(quinolin-8-yl)benzamides using di-tbutyldiaziridinone, leading to the formation of diverse anthranilic amides in good yields. The reaction likely proceeds through the generation of a pallada(II) heterocycle via aryl C-H activation, followed by amination with di-t-butyldiaziridinone.
Article
Chemistry, Multidisciplinary
Sanliang Li, Qiaoyu Chen, Junfeng Yang, Junliang Zhang
Summary: In this study, an efficient asymmetric gamma-arylation method for constructing chiral quaternary arylated butenolide was reported. The method showed high selectivity, good functional group tolerance, and excellent enantioselectivity. Additionally, it allowed for the facile construction of tricyclic tetrahydroindolines and tetrahydroisoquinolinones in one step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Hui-Ju Chen, Chien-Cheng Chiu, Tsui Wang, Dong-Sheng Lee, Ta-Jung Lu
Summary: The bis-NHC-Ag/Pd(OAc)(2) catalytic system is an intelligent catalyst that can efficiently reduce various functional groups to good to excellent yields, with high selectivity for different functional groups. In addition, the system can achieve stereoselective transformation of alkynes to alkenes in aqueous media, providing a simple operational protocol for reducing functional groups.
Article
Chemistry, Organic
Jianjun Wang, Huiying Hong, Daguo Hu, Jieling Liu, Wei Liu, Yian Shi
Summary: This work describes a Pd-catalyzed vinyl C-H amination reaction using di-t-butyldiaziridinone as a substrate, providing a variety of 3-amino-N-(quinolin-8-yl)acrylamides in good yield.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Valentina Beghetto, Vanessa Gatto, Silvia Conca, Noemi Bardella, Chiara Buranello, Giulia Gasparetto, Roberto Sole
CARBOHYDRATE POLYMERS
(2020)
Article
Biochemistry & Molecular Biology
Roberto Sole, Vanessa Gatto, Silvia Conca, Noemi Bardella, Andrea Morandini, Valentina Beghetto
Summary: The study demonstrates that CDMT/tert-amine systems are efficient and economical alternatives to conventional dehydro-condensation agents, showing high yields with reduced tert-amine consumption compared to other triazine quaternary ammonium salts.
Article
Chemistry, Organic
Roberto Sole, Lodovico Agostinis, Silvia Conca, Vanessa Gatto, Noemi Bardella, Andrea Morandini, Chiara Buranello, Valentina Beghetto
Summary: The development of new approaches that bypass harsh reaction conditions and hazardous chemicals is crucial. Novel compounds were synthesized, characterized, and tested for their reactivity in different experimental conditions, revealing a potential correlation between the chemical structure of the triazine compounds and their reactivity.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Applied
Roberto Sole, Alberto Scrivanti, Md Mahbubul Alam, Valentina Beghetto
Summary: The alkoxycarbonylation of trimethylsilylacetylene was studied to develop a sustainable synthesis of 2-(trimethylsilyl)acrylates. The choice of phosphine ligand had a significant impact on the reaction conditions, enabling high efficiency synthesis of the target product under milder conditions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Valentina Ferraro, Roberto Sole, Marco Bortoluzzi, Valentina Beghetto, Jesus Castro
Summary: The three-coordinated homoleptic Cu(I) complex with 2,6-dimethylphenyl isocyanide in the coordination sphere was easily synthesized and isolated as tetrafluoroborate salt. The complex is highly stable, active and selective toward the copper-catalyzed azide-alkyne cycloaddition, working in neat conditions and in the absence of bases at room temperature. Substrate scope was assessed by testing several different alkynes and azides, resulting in high yields of the corresponding 1,4-disubstituted-1,2,3-triazoles in most cases.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Andrea Morandini, Benedetta Leonetti, Pietro Riello, Roberto Sole, Vanessa Gatto, Isabella Caligiuri, Flavio Rizzolio, Valentina Beghetto
Summary: This study presents a simple method for synthesizing efficient, environmentally sustainable, and economically viable antibacterial products, and evaluates their antimicrobial efficacy against Staphylococcus aureus and Escherichia coli. The results indicate that these products can achieve total disinfection at certain concentrations, with lower cytotoxicity in the most effective compounds.
Article
Chemistry, Physical
Vanessa Gatto, Silvia Conca, Noemi Bardella, Valentina Beghetto
Summary: This study presents a simple protocol for collagen stabilization using CDET and a tertiary amine, resulting in high-quality leather with improved environmental performance. Different tertiary amines were tested in combination with CDET and the best performing condensation systems were further tested for cross-linking collagen powder and calf hides. The most successful results were achieved with CDET/NMM combination.
Review
Chemistry, Physical
Valentina Beghetto, Roberto Sole, Chiara Buranello, Marco Al-Abkal, Manuela Facchin
Summary: Currently, the scientific community is facing significant challenges in delivering a healthier world for future generations, with the quest for circular and sustainable approaches for plastic recycling being one of the most demanding. This is due to the large amounts of long-lasting waste generated by the massive use of plastic materials over the last century, particularly in packaging materials, which have not received adequate recovery and disposal policies for a long time.
Article
Chemistry, Physical
Roberto Sole, Chiara Buranello, Noemi Bardella, Alessandro Di Michele, Stefano Paganelli, Valentina Beghetto
Summary: A novel surfactant-type triazolyl-thioether ligand was prepared and showed excellent catalytic activity in the hydrogenation of various biomass-derived platform chemicals. The catalyst could be efficiently recycled up to 11 times, and in-depth analysis revealed the formation of spherical structures with metal nanoparticles surrounded by the ligand, preventing degradation.
Article
Green & Sustainable Science & Technology
Valentina Beghetto, Noemi Bardella, Riccardo Samiolo, Vanessa Gatto, Silvia Conca, Roberto Sole, Giacomo Molin, Andrea Gattolin, Nicola Ongaro
Summary: The study introduces a method for recycling polyolefin waste as efficient additives to produce hot mix asphalt, with modified HMA mixtures showing excellent performance compared to standard HMA in terms of density, stability, and other characteristics. The use of WOPO in HMA not only meets legal requirements for atmospheric emissions, but also has positive environmental and economic impacts on asphalt producers, recycling facilities, waste management costs, and greenhouse emissions.
JOURNAL OF CLEANER PRODUCTION
(2021)
Review
Polymer Science
Annamaria Visco, Cristina Scolaro, Manuela Facchin, Salim Brahimi, Hossem Belhamdi, Vanessa Gatto, Valentina Beghetto
Summary: Agri-food wastes are a significant issue both environmentally and economically. This review focuses on their potential use in producing building blocks for bioplastics or biofillers. Though there are EU-funded projects addressing this issue, challenges remain in labeling and separating bioplastics from fossil ones, as well as optimizing reuse before final composting and selective recovery.
Article
Chemistry, Physical
Roberto Sole, Jacopo Cappellazzo, Leonardo Scalchi, Stefano Paganelli, Valentina Beghetto
Summary: The one-pot alkoxycarbonylation reaction of halo-free alkylaryl and furanyl alcohols was investigated as a sustainable alternative for the synthesis of alkylaryl and furanyl acetates. By using benzyl alcohol as a model substrate, the reaction was tested under the presence of a homogeneous palladium catalyst, an activator, and a base. Various reaction parameters were studied, and it was found that the reaction conditions could be optimized to achieve high yields of the desired products. The study also extended to other substrates, including piperonyl and furfuryl alcohol, demonstrating the potential of this method for the synthesis of various fine chemicals.
Review
Environmental Sciences
Valentina Beghetto, Vanessa Gatto, Riccardo Samiolo, Cristina Scolaro, Salim Brahimi, Manuela Facchin, Annamaria Visco
Summary: The article provides an overview of EU policies, directives, regulations, and laws related to polymers and plastic manufacturing to reduce plastic pollution and understand the socio-economic implications of environmental concerns and protection.
ENVIRONMENTAL POLLUTION
(2023)
Article
Chemistry, Physical
Roberto Sole, Sofia Toldo, Marco Bortoluzzi, Valentina Beghetto
Summary: The unprecedented palladium catalysed carbonylation of benzyl acetate derivatives presented in this study allows for the synthesis of a broad range of alkyl arylacetates in excellent yields. This reaction does not require the use of halogen or base additives, and can be conducted under carbon monoxide ambient pressure, increasing its sustainability. The best performing catalyst was found to be the binary system palladium acetate (2 mol%)/DPPF (4 mol%), which demonstrated successful carbonylative transformations under specific conditions.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Andrea Morandini, Emanuele Spadati, Benedetta Leonetti, Roberto Sole, Vanessa Gatto, Flavio Rizzolio, Valentina Beghetto
Summary: This study presents the first examples of highly efficient antimicrobial triazine-derived bis imidazolium quaternary ammonium salts (TQAS), which were prepared with an easy, atom efficient, economically sustainable strategy and tested as antimicrobial agents with MIC values below 10 mg L-1. The TQAS demonstrated low MIC values and low cytotoxicity.
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
