Review
Crystallography
Weiqing She, Zhenzhen Xu, Lianjie Zhai, Junlin Zhang, Jie Huang, Weiqiang Pang, Bozhou Wang
Summary: Due to the introduction of oxygen atoms, N-oxide energetic compounds possess unique advantages in terms of oxygen balance, detonation properties, and energy density, which have attracted extensive attention from researchers worldwide. This article provides a comprehensive review of the synthetic strategies for two categories of N-oxides, azine N-oxides and azole N-oxides, and discusses the reaction mechanisms of aromatic N-oxide frameworks and their applications in creating high-energy substances. Furthermore, the energetic properties of N-oxide energetic compounds are compared and summarized.
Review
Chemistry, Multidisciplinary
Fengjuan Chen, Luo Liu, Wei Zeng
Summary: Compared with all-carbon parent compounds, incorporating Silicon into carboskeletons gives sila-analogues unique biological activity and physical-chemical properties. Silacycles have shown promising potential in biological chemistry, pharmaceuticals industry, and material chemistry. Therefore, the development of efficient methods to assemble versatile silacycles has been a topic of increasing concern. This review summarizes recent advances in the synthesis of silacycle-system, including transition metal-catalytic and photocatalytic strategies using various starting materials. The mechanistic aspects and features of these reaction methodologies are also highlighted.
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Organic
Qi-Wen Shen, Wei Wen, Qi-Xiang Guo
Summary: The first catalytic asymmetric cascade Heck-alkylation reaction of NH2-unprotected amino acid esters with N-(2-iodophenyl)allenamides is reported in this work. The reaction proceeds smoothly using a combining catalytic system comprising a chiral aldehyde, a chiral palladium complex, and the Lewis acid ZnCl2, giving optically active alpha-alkyl tryptophan derivatives in moderate to good yields and excellent enantioselectivities. The target products can be converted into other structurally complex chiral indoles without the loss of enantioselectivities.
Article
Chemistry, Organic
Lei Zhang, Bo Chen, Peipei He, Guosong Li, Lan-Cui Zhang, Shuang Gao
Summary: A series of polyoxometalate-ionic liquid catalysts have been developed to promote the Ritter reaction by introducing acidity and miscibility. Among them, [BSmim]CuPW12O40 [BSmim = 1-methyl-3-(4-sulfobutyl)-1H-imidazol-3-ium] displayed the highest activity for the amidation of alcohols with nitrites, delivering the corresponding amide products in good to excellent yields. Furthermore, the reaction can be easily scaled up to a gram scale without losing efficiency.
Article
Chemistry, Physical
Rok Narobe, Kathiravan Murugesan, Simon Schmid, Burkhard Koenig
Summary: This study presents a metal-free system based on iodine (I/III) catalytic manifold that can generate carbenium ion intermediates at electronically disfavored positions. The system exhibits unusually high reactivity due to the complexation of iodine (III) intermediates with BF3. Detailed mechanistic investigations suggest two possible pathways for the decarboxylative Ritter-type amination protocol.
Article
Chemistry, Organic
Youtian Fu, Ling Zhang, Maolin Sun, Liming Cao, Lei Yang, Ruihua Cheng, Yueyue Ma, Jinxing Ye
Summary: In this study, a practical and straightforward Ritter-type amination of electron-deficient aromatics was developed using electricity and sulfate. This method provides a series of acetanilides from simple electron-deficient arenes with moderate to good yields under mild conditions. It is characterized by cheap and readily available regents, atom and step economy.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Energy & Fuels
Mariyappan Vaithiyalingam, Chinnaperumal Kamaraj, Ramasamy Mohankumar, Sabarathinam Sarvesh, Paramasivam Deepak
Summary: The study found that imperatorin and its derivatives have potential pharmacological and insecticidal activities, showing good inhibitory effects against Staphylococcus aureus and Klebsiella pneumoniae. The modified compounds of imperatorin showed the best antibacterial activity and exhibited high larvicidal and pupicidal activities against larvae and pupae of Aedes aegypti.
BIOMASS CONVERSION AND BIOREFINERY
(2022)
Review
Chemistry, Organic
Meng-En Chen, Xiao-Wei Chen, Yue-Hong Hu, Rui Ye, Jian-Wei Lv, Baosheng Li, Fu-Min Zhang
Summary: This review article comprehensively surveys Ritter reactions from 2014 to 2020, discussing various types of reactions and their synthetic applications, including oxidative Ritter-type reactions, tandem Ritter reactions, and asymmetric Ritter reactions. It also systematically summarizes the application of Ritter reactions in total synthesis of natural products, as well as in the preparation of drugs, bioactive compounds, and functional molecules.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Cong-Hui Gao, Lei Yu, Xin-Yue Wu, Hong-Lin Wan, Wei Tan, Feng Shi
Summary: A tandem cyclization/addition reaction of 1,4-enediones with 2-naphthols was catalyzed by Bronsted acid, leading to the synthesis of a series of 2-furylmethylnaphthalenes with high yields (up to 98%). Control experiments provided insights into the possible reaction pathway and activation mode, contributing to the understanding of Bronsted acid catalysis and tandem reactions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Barbara C. Lemos, Eclair Venturini Filho, Rodolfo G. Fiorot, Fabrizio Medici, Sandro J. Greco, Maurizio Benaglia
Summary: This MiniReview compiles the most significant successful examples of highly efficient enantioselective catalytic protocols for the Povarov reaction since 2014, and provides a comprehensive discussion of different catalytic strategies employed in recent years. It also critically discusses the controversial dispute regarding the mechanistic pathways of this well-known reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Sandra Hernandez-Ibanez, Ana Sirvent, Miguel Yus, Francisco Foubelo
Summary: The stereocontrolled synthesis of 1-substituted homotropanones was achieved using chiral N-tert-butanesulfinyl imines as intermediates. Key steps in this methodology include the reaction of organolithium and Grignard reagents with hydroxy Weinreb amides, chemoselective N-tert-butanesulfinyl aldimine formation from keto aldehydes, decarboxylative Mannich reaction with beta-keto acids of these aldimines, and organocatalyzed L-proline intramolecular Mannich cyclization. The utility of the method was demonstrated with the synthesis of (-)-adaline and its enantiomer (+)-adaline.
Article
Chemistry, Multidisciplinary
Christina Jaeger, Mona Haase, Katja Koschorreck, Vlada B. Urlacher, Jan Deska
Summary: Biocatalytic oxidation of acylated hydroxylamines enables selective introduction of nitrogen functionalities by activating allylic C-H bonds. Utilizing laccases or oxidase/peroxidase couple with air as the oxidant, acylnitroso species are generated under mild aqueous conditions. These reactive intermediates undergo C-N bond formation through an ene-type mechanism, providing high yields in both intramolecular and intermolecular enzymatic aminations. Investigations on different pathways and labelling studies provide insight into the promiscuity of oxidoreductases as catalysts for nitroso-based transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Lucia Veltri, Roberta Amuso, Paola Vitale, Maria A. Chiacchio, Cinzia Benincasa, Bartolo Gabriele
Summary: A new process has been developed for the high value added conversion of carbon dioxide to 1,3-oxazine-2,4-diones through catalytic carboxylative heterocyclization of readily available 3-ynamides, yielding products in 44-85% yields under relatively mild conditions.
JOURNAL OF CO2 UTILIZATION
(2021)
Article
Chemistry, Organic
Subhash P. Chavan, Sanket A. Kawale, Rajesh G. Gonnade
Summary: The study presents a synthetic approach to achieve a novel intermediate of Tamiflu using cis-aziridine as a chiral building block and (D)-mannitol as a renewable starting material. The intramolecular Horner-Wadsworth-Emmons reaction is utilized as the key step for Tamiflu synthesis. However, the diene containing allylic aziridine framework is found to be inefficient in providing the core skeleton of Tamiflu through ring-closing metathesis reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Venkataraman Ganesh, Perali Ramu Sridhar, Srinivasan Chandrasekaran
ISRAEL JOURNAL OF CHEMISTRY
(2016)
Review
Chemistry, Organic
Venkataraman Ganesh, Srinivasan Chandrasekaran
SYNTHESIS-STUTTGART
(2016)
Article
Chemistry, Multidisciplinary
Devarajulu Sureshkumar, Venkataraman Ganesh, Naoya Kumagai, Masakatsu Shibasaki
CHEMISTRY-A EUROPEAN JOURNAL
(2014)
Article
Chemistry, Organic
Venkataraman Ganesh, Adam Noble, Varinder K. Aggarwal
Article
Chemistry, Organic
Venkataraman Ganesh, Taraknath Kundu, Srinivasan Chandrasekaran
Article
Chemistry, Organic
Charlotte H. U. Gregson, Venkataraman Ganesh, Varinder K. Aggarwal
Review
Chemistry, Organic
Sourav Mondal, Tamal Ballav, Krishna Biswas, Suman Ghosh, Venkataraman Ganesh
Summary: Palladium-catalyzed cascade reactions have gained much attention in organic synthesis for their efficiency and rapid transformation, serving as a powerful tool for multiple bond formations and reducing cost and time. With a wide range of functional group tolerance, these reactions have been successful in synthesizing complex molecules with biological relevance.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Applied
Krishna Biswas, Aniruddha Das, Venkataraman Ganesh
Summary: Organophosphorus catalysis has become a robust platform for introducing boron and silicon functionalities into organic substrates, providing efficient synthetic methodologies. Phosphorus compounds efficiently catalyze various reactions such as hydroboration and silylation in different organic substrates, with the classification of nucleophilic, electrophilic, and biphilic phosphorus catalysts.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Organic
Tamal Ballav, Rajesh Chakrabortty, Aniruddha Das, Suman Ghosh, Venkataraman Ganesh
Summary: This review summarizes the research achievements in the field of synergistic dual catalysis in recent years, highlighting the unique strategies of carbon-carbon and carbon-heteroatom bond formation achieved by combining Pd catalyst with transition metals, Lewis acids, or organocatalysts. The wide applications of these strategies in pharmaceutical and agrochemical industries are also discussed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Suman Ghosh, Rajesh Chakrabortty, Shailendra Kumar, Aniruddha Das, Venkataraman Ganesh
Summary: This paper presents the protoboration of 1,3-diynes as a platform for the iterative functionalization of various groups on enynes and dienes. Synthetic approaches to targets with high complexity are directed toward using small, modular building blocks similar to a Lego construction using iterative chemistry and automated synthesis. Organoboron compounds are currently in the spotlight for achieving these goals. Here, we report an operationally simple, regioselective protoboration of 1,3-diynes using a mixed diboron reagent and Cu(I)/phosphine catalyst to provide enynylboronates in good yields. Under similar conditions, diprotoboration of 1,3-diynes was also achieved to access bench-stable 1,4-diboryl-1,3-dienes in good yields and regioselectivities. The iterative coupling capabilities of the products have been demonstrated along with other downstream transformations offering a range of value-added skeletons.
Article
Chemistry, Organic
Sourav Mondal, Tamal Ballav, Tofayel Sheikh Mohammad, Venkataraman Ganesh
Summary: We present the synthesis and characterization of bis-benzofulvenes, as well as their optical and redox properties. The bis-benzofulvenes were synthesized through Pd-catalyzed intramolecular Heck coupling and Ni(0)-mediated C-(sp(2))-Br dimerization. By tuning the substituents on the exomethylene unit and the aromatic ring, we achieved low optical and electrochemical energy gaps of 2.05 and 1.68 eV. The trends in the energy gaps were compared, and the frontier molecular orbitals were visualized using density functional theory.
Article
Chemistry, Physical
Suman Ghosh, Rajesh Chakrabortty, Shailendra Kumar, Aniruddha Das, Venkataraman Ganesh
Summary: This paper presents a method for protoboration, achieving the synthesis of complex target structures, as well as operationally simple and regioselective reaction conditions for the preparation of products with added value.
Review
Chemistry, Multidisciplinary
Aankhi Khamrai, Venkataraman Ganesh
Summary: This review tracks the journey of free radicals from being uncontrollable to emerging as a powerful tool in chemistry. A modern perspective on the generation of radicals is offered, with a focus on unique strategies in catalyzing radical reactions.
JOURNAL OF CHEMICAL SCIENCES
(2021)
Article
Chemistry, Multidisciplinary
Claire M. Wilson, Venkataraman Ganesh, Adam Noble, Varinder K. Aggarwal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
Article
Chemistry, Multidisciplinary
Venkataraman Ganesh, Marcin Odachowski, Varinder K. Aggarwal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)