Review
Chemistry, Multidisciplinary
Kuntal Pal, Chandra M. R. Volla
Summary: Alpha-imino carbenoids generated via transition metal catalyzed denitrogenative ring-opening of N-sulfonyl-1,2,3-triazoles have found extensive applications in synthetic organic chemistry over the past decade. In addition, 3-diazoindolin-2-imines have been successfully used as alternative sources of alpha-imino carbenoid precursors for the development of methodologies to access diverse indole derivatives. This review summarizes the insertion reactions of alpha-imino metal carbenes derived from N-sulfonyl-1,2,3-triazoles and 3-diazoindolin-2-imines.
Article
Chemistry, Multidisciplinary
Li Li, Chenggang Mi, Guanwang Huang, Meirong Huang, Yuyi Zhu, Shao-Fei Ni, Zhaofeng Wang, Yong Huang
Summary: In this study, a new approach based on an I(III)/S(VI) reagent is described, which enables the cascade insertion of heteroatoms by sequentially generating two α-heteroatom-substituted metal carbenes in one reaction. This method allows for the synthesis of a wide range of α,α-O,O-, α,α-O,N-, and α,α-N,N-substituted ketones under mild conditions, and demonstrates the ability to simultaneously introduce multiple functional groups.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ming-Yao Huang, Shou-Fei Zhu
Summary: In comparison to common carbene insertion reactions, the overlooked uncommon carbene insertion reactions have been gaining more attention recently for their synthetic potential. The perspective reviews the history and latest advances of uncommon carbene insertion reactions, discusses their potential applications and challenges, and provides an outlook for this promising field.
Article
Chemistry, Organic
Nansalmaa Otog, Soda Chanthamath, Ikuhide Fujisawa, Seiji Iwasa
Summary: The Ru(II)-Pheox catalyzed B-H bond insertion reactions of alpha-methyl diazoesters with phosphine- and amine-borane adducts were successfully developed. A unique alpha-methyl diazoester (dinaphthylenyl diazopropionate) showed the highest enantioselectivity, and a newly synthesized dinaphthylenyl diazophenylacetate led to improved yield and enantioselectivity of the carbene transfer B-H insertion reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Cheng Yi, Hu Rongjing, Chen Xiaoqi, Yang Hao, Niu Xiaokang, Yang Lei
Summary: This article summarizes the research progress of direct catalytic silylation of C(sp(3))-H bonds and discusses the mechanism and application range of related reactions.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Applied
Artem A. Antonov, Konstantin P. Bryliakov
Summary: This review surveys recent progress in transition metal catalyzed, metal-free, and electrochemical selective acyloxylations of C(sp3)-H bonds, covering modifications of different substrate types and discussing their synthetic potential, as well as correlations between catalyst nature, oxidant, additives, conditions, and acyloxylation regio- and chemoselectivity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Review
Chemistry, Physical
Ximei Zhao, Guanghui Wang, A. Stephen K. Hashmi
Summary: Carbene B-H insertion reactions, including free and metal carbene insertion into B-H bonds, have made significant advances in recent years. The development of this chemistry complements existing C-B bond formation strategies in terms of substrate scope, selectivity, and product diversity. Notably, catalytic enantioselective carbene B-H insertion reactions enable easy access to important chiral organoboron compounds.
Review
Biochemistry & Molecular Biology
Naoya Onishi, Ryoichi Kanega, Hajime Kawanami, Yuichiro Himeda
Summary: This article provides an overview of recent advances in the research on hydrogen generation by formic acid dehydrogenation, focusing primarily on the development of homogeneous catalysts, which can accelerate the transition to a hydrogen-based society.
Article
Chemistry, Physical
Yu-Xuan Su, Ming-Yao Huang, Shou-Fei Zhu
Summary: Amino acids, as the building blocks of proteins, play crucial roles in various fields such as synthetic chemistry, medicinal chemistry, and materials chemistry. While natural amino acids can be obtained from living organisms, synthetic methods are necessary for unnatural amino acids. A recent method utilizing asymmetric N-H bond carbene insertion reaction with α-diazoacetates has demonstrated high enantioselectivity and good functional group tolerance, enabling the facile synthesis of both natural and unnatural amino acids and introducing new concepts in catalysis.
Review
Chemistry, Inorganic & Nuclear
Baokang Geng, Lingling Zhang, Fei Wang, Xiao Wang, Shuyan Song, Hongjie Zhang
Summary: Single-atom-alloy catalysts (SAAs) can improve the dispersion ratio of noble metals on another metal surface, while maintaining excellent heterogeneous catalytic performance. SAAs not only benefit from the metal bonds between noble metals and support metals, but also provide unique catalytic performance by constructing metallic metal single atoms. Recently, SAAs have been demonstrated to catalyze significant heterogeneous reactions. This review will discuss the synthesis methods of SAAs and summarize their applications in heterogeneous catalysis.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Hui-Na Zou, Yu-Tao Zhao, Liang-Liang Yang, Ming-Yao Huang, Jing-Wei Zhang, Meng-Lin Huang, Shou-Fei Zhu
Summary: Chiral propargylic boron compounds have a wide range of potential applications, but the synthesis of these compounds with high enantioselectivity is still unknown. This study reports a catalytic method for the construction of chiral propargylic boron compounds with high enantioselectivity.
Review
Chemistry, Multidisciplinary
Dimitrios K. Perivoliotis, Joakim Ekspong, Xue Zhao, Guangzhi Hu, Thomas Wagberg, Eduardo Gracia-Espino
Summary: To meet the demand for clean energy production, the development of advanced electrocatalysts for water splitting has gained increasing attention. Non-noble metal catalysts based on transition metals and light elements have shown improved performance. By introducing defects, the catalytic performance of these materials can be further enhanced. This review critically summarizes the latest progress on the role of defects in catalytic electrolysis applications, covering a broad class of nanomaterials.
Review
Chemistry, Multidisciplinary
Vatcharaporn Aomchad, Alex Cristofol, Francesco Della Monica, Bart Limburg, Valerio D'Elia, Arjan W. Kleij
Summary: Biomass-related feedstock can be used as a coupling partner with CO2, allowing the development of more functional and complex carbonate architectures. This development has become an important part of new and more sustainable material designs in recent years.
Review
Chemistry, Organic
Yang Xing, Liu Xu, Wang Lijia
Summary: Transition metal-catalyzed activation of C(sp3)-H bonds to form carbon-nitrogen bonds is a challenging and hot research area. The C(sp3)-H amination strategy provides a more direct and efficient way to form C-N bonds. Various directing groups and transition metal catalyst systems have been developed, allowing for effective C(sp3)-H amination through the inner sphere mechanism. Recent progress in directing group-assisted C(sp3)-H bond amination reactions, using catalyst systems based on different transition metals and inexpensive amination reagents, is reviewed in this article.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Green & Sustainable Science & Technology
Tongtong Zhang, Joao Uratani, Yixuan Huang, Lejin Xu, Steve Griffiths, Yulong Ding
Summary: The global energy sector is responsible for 75% of total greenhouse gas emissions. Hydrogen, a low-carbon energy carrier, is considered crucial for transitioning to a decarbonized energy system. The concept of a hydrogen economy is seen as a key part of this transition. Liquid hydrogen, due to its high energy density, ambient storage pressure, purity, and mature technology, is suitable for long-distance transport and has gained increased attention. However, challenges such as energy-intensive liquefaction and hydrogen boil-off losses hinder the development of the liquid hydrogen system. This review focuses on the current state of technology related to the liquid hydrogen supply chain and discusses its potential role in the emerging global hydrogen economy.
RENEWABLE & SUSTAINABLE ENERGY REVIEWS
(2023)
Review
Chemistry, Organic
Virginie Carreras, Nour Tanbouza, Thierry Ollevier
Summary: The use of iron catalysis in reactions involving diazo compounds has become increasingly popular, offering a valuable alternative to toxic and expensive metal catalysts. Iron-mediated reactions have shown great potential in forging carbon-carbon or carbon-heteroatom bonds through insertion reactions, ylide formation, and other methods.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Samuel Lauzon, Lionel Schouwey, Thierry Ollevier
Summary: A chiral ligand was successfully synthesized and its structure and configuration were determined by single-crystal diffraction analysis. The newly synthesized ligand displayed excellent catalytic activity and selectivity in iron-catalyzed asymmetric reactions.
Article
Chemistry, Organic
Nour Tanbouza, Laurent Caron, Azadeh Khoshoei, Thierry Ollevier
Summary: A new bismuth(V) oxidative catalytic system has been developed and applied for the conversion of hydrazones into diazo compounds, achieving excellent yields.
Article
Chemistry, Organic
Nour Tanbouza, Alessia Petti, Matthew C. Leech, Laurent Caron, Jamie M. Walsh, Kevin Lam, Thierry Ollevier
Summary: An electrochemical synthesis method was developed for the efficient conversion of hydrazones into diazo compounds, achieving yields as high as 99%. This method was shown to be both environmentally friendly and practical, as it required mild conditions and demonstrated high electron efficiency (3 F/mol) comparable to commonly used chemical oxidants.
Review
Chemistry, Organic
Hoang-Minh To, Oleksii Malets, Maryna Mazur, Olha Mykhailenko, Olena Kompaniiets, Thierry Ollevier
Summary: Halodiazirines, as important reagents, have been widely applied in photochemical and thermal cyclopropanation reactions. This article reviews the synthetic applications of Halodiazirines as halocarbene precursors in various reactions with alkenes.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Applied
Maryne A. J. Dubois, Virginie Carreras, Matt R. Adams, Vanessa Kairouz, John G. Riley, Jean-Francois Vincent-Rocan, Andre B. Charette
Summary: The importance of rapid access to diagnostics tools, including bioreagents, for pathogen identification has been highlighted in the COVID-19 pandemic. A telescoped continuous flow synthesis of DTT has been developed, involving a base-mediated ring closure epoxidation, a nucleophilic epoxide opening, and an acid-mediated deacetylation. This method allows in situ generation and consumption of the hazardous intermediate, minimizing the need for isolation and improving safety.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2023)
Article
Chemistry, Multidisciplinary
Zaineb Litim, Hanen Slimi, Thierry Ollevier, Jamil Kraiem
Summary: A green and catalyst-free method was developed for the synthesis of N-sulfonylimines, which involved the condensation of sulfonamides with aldehydes using neutral Al2O3 as a reusable dehydrating agent. The method provided high yielding and pure N-sulfonylimines under simple experimental conditions.
Editorial Material
Chemistry, Organic
Thierry Ollevier
Article
Chemistry, Organic
Houda Bouchnak, Thierry Ollevier, Jamil Kraiem
Summary: A new, simple, and efficient method for the synthesis of 3-aminohydantoins was developed, starting from commercially available alpha-amino esters. The method offers a practical and straightforward protocol to obtain the desired compounds in moderate to good yields.
Article
Chemistry, Multidisciplinary
Hanen Slimi, Zaineb Litim, Thierry Ollevier, Jamil Kraiem
Summary: This article introduces a new catalytic method for the symmetrical and nonsymmetrical etherification of benzyl alcohols. In the symmetrical etherification reaction, FeCl36H(2)O is used as the catalyst and propylene carbonate is used as a solvent. In the nonsymmetrical etherification reaction, FeCl24H(2)O and pyridine bis-thiazoline ligand are used as catalysts. These methods have eco-friendly conditions.
Review
Chemistry, Multidisciplinary
Samuel Lauzon, Thierry Ollevier
Summary: This review provides an overview of the significant applications of fluorine-containing ligands reported in literature from 2001 to mid-2021. The ligands are classified based on the nature of donor atoms involved. The review highlights metal-ligand interactions and the structure-reactivity relationships resulting from the presence of fluorine atom or fluorine-containing substituents on chiral catalysts.
Article
Chemistry, Multidisciplinary
Riccardo Pedrazzani, Emanuele Pinosa, Giulio Bertuzzi, Magda Monari, Samuel Lauzon, Thierry Ollevier, Marco Bandini
Summary: A new Au(i) catalyzed intramolecular hydrocarboxylation of allenes is presented, which serves as a valuable synthetic route to oxazino-indolones. The use of 3,5-(CF3)(2)-C6H3-ImPyAuSbF(6) as the optimal catalyst allows for wide tolerance of functional groups, mild reaction conditions, and high yields. Preliminary attempts towards an enantioselective version are also documented using a new family of chiral C-1-symmetric ImPyAuCl complexes.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Thierry Ollevier, Virginie Carreras
Summary: Aryl trifluoromethyl diazoalkanes and diazirines have become unique reactants in synthetic methodology. Highlighted for their versatility in applications towards a wide range of synthetic transformations, these compounds, bearing CF3 groups and accessible for synthesis, are valuable as precursors of stabilized metal carbenes.
ACS ORGANIC & INORGANIC AU
(2022)
Article
Chemistry, Multidisciplinary
Samuel Lauzon, Thierry Ollevier
Summary: By designing a novel chiral ligand, high levels of stereoselectivity can be achieved in synthetic reactions. The unique properties of the new ligand can enhance both reaction yields and enantioselectivities.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)