Article
Chemistry, Organic
Bruno Lainer, Dawid Lichosyt, Maiia Aleksandrova, Pawel Dydio
Summary: In this study, an enantioselective synthesis of secondary benzylic alcohols and diarylmethanols was achieved through sequential catalysis, allowing for various alcohols and aryl nucleophiles with tolerance to a range of functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Renshi Luo, Jinghui Tong, Lu Ouyang, Liang Liu, Jianhua Liao
Summary: The formation of C-N bond is crucial in creating molecular diversity, and this paper presents a new strategy for synthesizing secondary amines through iridium-catalyzed one-pot reductive amination. The method demonstrates compatibility with various carbonyl compounds, delivering desired products in good yields under mild conditions.
Article
Chemistry, Organic
Zakhar M. Rubanov, Vitalij V. Levin, Alexander D. Dilman
Summary: This paper describes a method for converting aldehydes to ketones by first forming aldimines, and then utilizing acid-promoted Minisci-type reaction with alkyl radicals generated from esters of N-hydroxylphthalimide under photoredox conditions. Aminyl radical cations formed after the addition of the iminium ions are believed to be key intermediates.
Article
Chemistry, Multidisciplinary
Leijing Chen, Zhen Wang, Hui Liu, Xinyue Li, Bin Wang
Summary: A metal-free radical cyclization/dehydrogenation cascade of alkenes with aldehydes has been developed for the synthesis of 3,5-disubstituted isoxazoles in a one-pot system. This protocol features excellent functional group tolerance and operational simplicity, and is easily scaled up.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Juntao Yang, Bingxian Liu, Junbiao Chang
Summary: A ruthenium(II)-catalyzed one-pot synthesis of highly substituted 1,2-dihydropyridines (DHPs) via a three component reaction system has been successfully developed. The reaction utilizes a simple Ru(II) catalyst without the need for specific ligands. The catalytic system shows excellent functional group compatibility with a wide range of starting materials. The obtained DHPs can be easily converted into tetrahydropyridines and azabicyclo[4.2.0]octa-4,7-dienes by subsequent reduction or [2 + 2] cycloaddition reaction.
Article
Chemistry, Organic
Devaneyan Joseph, Myeong Seong Park, Sunwoo Lee
Summary: N-Acyl lactam amides reacted with amines in the presence of DTBP and TBAI under aqueous conditions to afford transamidated products with good yields and functional group tolerance. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions, suggesting a radical reaction pathway.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Shihaozhi Wang, Jiale Yang, Dianjun Li, Jinhui Yang
Summary: A novel tandem N-dealkylation and N-methyl aerobic oxidation of tertiary aromatic amines to N-arylformamides using copper and TEMPO has been developed, providing an alternative synthetic route from N-methylarylamines to N-arylformamides.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Zhi-Cheng Yu, You Zhou, Xiang-Long Chen, Jin-Tian Ma, Li-Sheng Wang, Yan-Dong Wu, An-Xin Wu
Summary: A reductive coupling reaction was established for the synthesis of diaryl 1,2-dicarbonyl compounds from aryl methyl ketones. The reaction involves C(CO)-C(sp3) bond cleavage and proceeds through an electron transfer process. Notably, this reaction is simple to operate, has mild reaction conditions, and is applicable to a wide range of substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Xiaoyu Yang, Liang Wang, Fangzhi Hu, Lubin Xu, Sanming Li, Shuai-Shuai Li
Summary: The switchable synthesis of 3-non, 3-mono, 3,3'-disubstituted 3,4-dihydroquinolin-2(1H)-ones was achieved using a redox-neutral hydride-transfer/N-dealkylation/N-acylation strategy. This unprecedented method allowed for the synthesis of highly functionalized products with in situ utilization of released HCHO via o-QM involved Michael addition, showcasing the synthetic utility of the protocol for concise synthesis of CYP11B2 inhibitor.
Article
Chemistry, Organic
Jin Zhang, Pei Zhang, Yangmin Ma, Michal Szostak
Summary: This study reports a novel solvent-free method for synthesizing ketones with high selectivity from acyl chlorides and boronic acids. The reaction takes place in the solid state, without the use of solvents, and has a short reaction time, demonstrating excellent selectivity for C(acyl)-Cl bond cleavage.
Article
Chemistry, Organic
Narasingan Aravindan, Masilamani Jeganmohan
Summary: An efficient synthesis of benzo-[c]-phenanthridine alkaloids via a synergistic combination of C-C bond formation and a cycloaromatization reaction is described. Aryl nitrones react with 7-azabenzonorbornadienes in the presence of a Rh-(III) catalyst, providing pharmaceutically useful benzo-[c]-phenanthridine derivatives in good to moderate yields. Using this methodology, highly useful alkaloids such as norfagaronine, norchelerythrine, decarine, norsanguinarine, and nornitidine were prepared in a single step.
Article
Chemistry, Organic
Meng-Hui Li, Xiao-Ju Si, He Zhang, Dandan Yang, Jun-Long Niu, Mao-Ping Song
Summary: An efficient cobalt-catalyzed three-component coupling reaction is disclosed, which can construct C(sp(2))-C(sp(3)) and C-O bonds in one-pot with high yields and functional group compatibility. Mechanistic studies suggest a radical process may be involved in the reaction.
Article
Chemistry, Multidisciplinary
Han Gao, Lingfei Hu, Yanlei Hu, Xiangying Lv, Yan-Bo Wu, Gang Lu
Summary: The origins of regioselectivity in Ni-catalyzed alkene hydrofunctionalizations were computationally investigated using energy decomposition analysis. The results indicate that the Markovnikov selectivity with aryl-substituted alkenes is favored due to the stabilizing charge transfer effect, while the anti-Markovnikov selectivity with alkyl-substituted alkenes is favored because of the destabilizing Pauli repulsion effect.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Hui Chen, Tianhua Tang, Christian A. Malapit, Yoo Seok Lee, Matthew B. Prater, N. Samali Weliwatte, Shelley D. Minteer
Summary: Petroleum hydrocarbons are a major energy source and an important feedstock for the chemical industry. The deep conversion of inert hydrocarbons to more valuable chemicals is a significant challenge. In this study, a multistep bioelectrocatalytic system was developed to achieve the one-pot deep conversion of heptane to N-heptylhepan-1-imine. This system successfully realized the conversion of inert hydrocarbons to imines, providing a new methodology for the comprehensive conversion and utilization of inert hydrocarbons.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yi-Fan Zhang, Han-Nan Chen, Yi Xiao, Zhencun Cui, Wei David Wang, Guo-Qiang Xu
Summary: Here, a novel protocol for synthesizing alpha-functionalized saturated aza-heterocycles is presented, allowing for the easy installation of various nucleophilic groups. Additionally, a range of biologically valuable 3,3'-diindolylmethane derivatives can be readily synthesized under mild photocatalytic conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Rita Mocci, Evelina Colacino, Lidia De Luca, Claudia Fattuoni, Andrea Porcheddu, Francesco Delogu
Summary: The Beckmann rearrangement, discovered over a century ago, remains compliant with green chemistry principles and sustainable development aspects. A sustainable mechanochemical procedure was developed to design new amide frameworks via a cut-and-paste process on the oxime backbone, utilizing inexpensive reagents to prepare various amides, including marketable compounds like epsilon-caprolactam and the API paracetamol, in good to high yields. This solvent-free procedure was also successfully extended to ketones serving as oxime precursors.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2021)
Article
Chemistry, Multidisciplinary
Or Galant, Giacomo Cerfeda, Aaron S. McCalmont, Stuart L. James, Andrea Porcheddu, Francesco Delogu, Deborah E. Crawford, Evelina Colacino, Sabrina Spatari
Summary: The scale-up of mechanochemical methods has the potential to make manufacturing processes in the pharmaceutical industry greener by eliminating the use of solvents. The study evaluates the sustainability and green chemistry metrics for producing nitrofurantoin via mechanochemical continuous twin-screw extrusion and conventional solvent-batch synthesis methods. The results show significant reductions in energy, climate change, and cost for the mechanochemical method, while maintaining high product selectivity.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Swapneel Thakkar, Lidia De Luca, Silvia Gaspa, Alberto Mariani, Sebastiano Garroni, Antonio Iacomini, Luigi Stagi, Plinio Innocenzi, Luca Malfatti
Summary: Graphene-enhanced Raman scattering (GERS) is a chemical-based enhancement of Raman signal. Graphene nanostructures can be used to build a platform for fast and sensitive detection of pesticides in water. The properties of graphene nanostructures affect GERS performance, with monolayers being more efficient than few-layer structures. Surface functionalization reduces GERS effect.
Review
Biochemistry & Molecular Biology
Federico Casti, Francesco Basoccu, Rita Mocci, Lidia De Luca, Andrea Porcheddu, Federico Cuccu
Summary: Chemists have changed their approach to organic molecule synthesis in recent years by adopting greener reagents, solvents, and methodologies that consider environmental issues such as water, soil, and air pollution. The utilization of plant and animal derivatives, usually considered as waste material, has led to the development of new green strategies. This review highlights the important innovations in this field, with a focus on materials such as wool, silk, feather, and proteins and their derivatives, which play a crucial role in organic reactions.
Article
Chemistry, Organic
Francesco Basoccu, Federico Cuccu, Federico Casti, Rita Mocci, Claudia Fattuoni, Andrea Porcheddu
Summary: Isocyanides, although difficult to produce and handle, are valuable compounds for accessing sophisticated synthetic routes. This paper presents a conceptually innovative synthetic protocol for mechanochemical isocyanide preparation, aiming to reduce reagent toxicity and improve purification processes.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Federico Cuccu, Lidia De Luca, Francesco Delogu, Evelina Colacino, Niclas Solin, Rita Mocci, Andrea Porcheddu
Summary: Mechanochemical transformations have revolutionized the field of chemistry, particularly in organic synthesis, by challenging traditional concepts and opening up new reaction paths.
Article
Chemistry, Organic
Federico Casti, Rita Mocci, Andrea Porcheddu
Summary: Two easily accessible methods for preparing a variety of formylated and acetylated amines under mechanochemical conditions are presented. These two methodologies have complementary features, as they allow for the derivatization of aliphatic and aromatic amines.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Federico Cuccu, Francesco Basoccu, Claudia Fattuoni, Andrea Porcheddu
Summary: This article presents a mechanochemical acylation procedure based on acyl-saccharin derivatives, providing a valuable solvent-free alternative with rapid and user-friendly workup for multi-step procedures.
Article
Chemistry, Applied
Silvia Gaspa, Luca Ledda, David d'Atri, Andrea Porcheddu, Luisa Pisano, Massimo Carraro, Lidia De Luca
Summary: An esterification of the C-H bond of aldehydes is achieved using oxidovanadium(IV) sulfate as a catalyst. The reaction is facilitated by visible-light irradiation, performed at room temperature, and requires no additives, with H2O2 as the benign oxidant. This study showcases the potential of vanadium salts in halogenation processes, C-H activation, and contributes to the field of earth-abundant metal-based catalysis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Francesco Basoccu, Federico Cuccu, Pietro Caboni, Lidia De Luca, Andrea Porcheddu
Summary: The synthesis of nitrogen-based heterocycles is crucial for pharmaceutical and agricultural development. However, current methods often involve harsh conditions or the use of toxic solvents and reagents. Mechanochemistry offers a promising solution by reducing environmental impact. In this study, we propose a new mechanochemical protocol that utilizes thiourea dioxide to synthesize various heterocyclic moieties, providing a more sustainable and eco-friendly approach.
Article
Chemistry, Multidisciplinary
Francesco Basoccu, Federico Cuccu, Andrea Porcheddu
Summary: Nitroso derivatives with unique characteristics have been extensively studied in various fields, including biology and clinical research. This study demonstrates a mechanochemical procedure for synthesizing nitroso compounds under solid-state conditions and successfully synthesizes previously unknown compounds with potential biological and pharmaceutical applications.
Review
Chemistry, Multidisciplinary
Nicolas Fantozzi, Jean-Noel Volle, Andrea Porcheddu, David Virieux, Felipe Garcia, Evelina Colacino
Summary: This article highlights the significance of green chemistry methods for promoting sustainable development, with a focus on batch and continuous mechanochemical methods in organic synthesis. The environmentally-friendly aspects of these methods are objectively assessed using green metrics and indicators, providing a comprehensive evaluation of their greenness. The article also provides an introduction to the topic, discusses variables influencing reaction outcomes, and offers an outlook for future research in this field.
CHEMICAL SOCIETY REVIEWS
(2023)
Article
Chemistry, Multidisciplinary
Andrea Porcheddu, Rita Mocci, Margherita Brindisi, Federico Cuccu, Claudia Fattuoni, Francesco Delogu, Evelina Colacino, Maria Valeria D'Auria
Summary: An environmentally friendly mechanochemical protocol was developed to synthesize indoles and indolines using oxalic acid and dimethylurea. The solvent-free procedure showed versatility and wide scope, leading to variously decorated compounds. The methodology also has potential for preparing compounds of pharmaceutical interest.
Article
Chemistry, Physical
Maria Carta, Francesco Delogu, Andrea Porcheddu
Summary: Mechanochemistry offers new and greener synthetic routes by enabling solvent-free chemical reactions, and understanding the relationships between processing variables, powders' mechanical behavior, and chemical reactivity is crucial for its practical exploitation. A phenomenological kinetic model proposed in this work can help experimentalists decipher the mechanical, chemical, and statistical factors underlying mechanochemical reactions, providing insights into the underlying mechanochemistry through satisfactorily fitting experimental datasets with the model equations.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2021)
Article
Chemistry, Physical
Gabriele Traversari, Andrea Porcheddu, Giorgio Pia, Francesco Delogu, Alberto Cincotti
Summary: Driven by the promise of alternative synthetic routes, mechanochemistry is experiencing rapid growth in utilizing mechanical forces to develop solvent-less processes for greener chemical industry. A kinetic model is developed in this study, taking into account the statistical nature of mechanical processing of powders, combining rheological behavior of molecular solids and interface reactions. This model provides a comprehensive overview of the kinetic scenario in mechanochemical processes, showing how factors such as statistical, mixing, and chemical elements affect the kinetics.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2021)
