Article
Chemistry, Multidisciplinary
Mingyu Liu, Tianhua Tang, Omar Apolinar, Rei Matsuura, Carl A. Busacca, Bo Qu, Daniel R. Fandrick, Olga Zatolochnaya, Chris H. Senanayake, Jinhua J. Song, Keary M. Engle
Summary: This method presents a selective and catalytic approach for synthesizing 1,3-enynes without the need for prefunctionalized building blocks, allowing for highly regio- and stereoselective formation of the target products. It is versatile, scalable, and can operate effectively with as low as 0.5 mol % catalyst loading. Preliminary mechanistic experiments support a redox-neutral Pd(II) catalytic cycle.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Physical
Stefan Weber, Luis F. Veiros, Karl Kirchner
Summary: Efficient manganese-catalyzed dimerization of terminal alkynes to produce 1,3-enynes is achieved in this study. The reaction is atom economic, utilizing an inexpensive catalyst with high efficiency and selectivity.
Article
Chemistry, Organic
Pete Delgado, Raoul J. Glass, Gina Geraci, Rohit Duvadie, Dyuti Majumdar, Richard Robinson, Imran Elmaarouf, Malte Mikus, Kian L. Tan
Summary: Facilitating photoredox coupling reactions in process-friendly green solvents was achieved by the successful application of a dual Ir/Ni catalyst system with enhanced solubility properties. This presentation highlights the benefits of altering the solubility properties of the ligands used in the Ir/Ni dual catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber
Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Zhenghong Zhou, Jimin Yang, Bo Yang, Yang Han, Lijuan Zhu, Xiao-Song Xue, Feng Zhu
Summary: This study presents a pioneering example of nickel-catalysed enantioconvergent Stille cross-coupling reactions. The reactions result in the formation of C-C bonds in good to high yields with excellent stereoselectivity, providing a practical and cost-effective method for synthesis. The innovative use of synergistic photoredox/nickel catalysis enables a novel single-electron transmetalation process, opening up new research possibilities in the field of Stille reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Lilian Geniller, Marc Taillefer, Florian Jaroschik, Alexis Prieto
Summary: The Ni-photoredox catalyzed desulfurative cross-coupling reaction enables the synthesis of various unsymmetrical diarylmethane molecules under mild reaction conditions, providing new transformations of abundant, naturally occurring thiols.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Lixin Liu, Jianyu Dong, Zuqi Fu, Lebin Su, Shaofeng Wu, Qian Shang, Shuang-Feng Yin, Yongbo Zhou
Summary: In this study, a specific cross-dimerization of terminal alkynes is developed under Pd/TMEDA catalysis, which produces a series of gem-1,3-enynes with different functional group tolerance in moderate to high yields. The reaction features anti-addition-carbometallation, easy control of selectivity, wide range of donor alkynes, and simple catalytic conditions.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Physical
Jordan L. S. Zackasee, Samir Al Zubaydi, Blaise L. Truesdell, Christo S. Sevov
Summary: Mediator-assisted electrocatalysis is a general strategy to enhance the electroreductive cross-electrophile coupling (eXEC) reactions. Addition of a redox-matched mediator enables the catalyst-mediator systems to generate products in near-quantitative yield. This study also identifies a library of catalyst-mediator systems that can couple a wide range of substrate classes in high yields.
Article
Chemistry, Multidisciplinary
Dejiang Zhang, Liyuan Le, Renhua Qiu, Wai-Yeung Wong, Nobuaki Kambe
Summary: A strategy for the formation of antimony-carbon bond via nickel-catalyzed cross-coupling of halostibines was developed. This method has a wide substrate scope and is compatible with various functional groups. The successful synthesis of arylated stibine demonstrated the high synthetic potential of this transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Ayan Dasgupta, Katarina Stefkova, Rasool Babaahmadi, Brian F. Yates, Niklaas J. Buurma, Alireza Ariafard, Emma Richards, Rebecca L. Melen
Summary: The donor-acceptor ability of frustrated Lewis pairs has been widely used in organic synthesis. Single electron transfer can generate a frustrated radical pair, leading to different reaction pathways and selectivity depending on the substrate and energy required. Investigation using EPR studies, kinetic studies, and DFT calculations has helped elucidate the mechanism of these coupling reactions and explain solvent-dependent site selectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Review
Chemistry, Multidisciplinary
You Wang, Yuli He, Shaolin Zhu
Summary: Migratory cross-coupling via metal migration is a significant process in academic and industrial fields, providing an attractive alternative for the synthesis of challenging structures. This Account outlines recent progress and developments in the field, including migration-functionalization modes, diverse functionalizations, and strategies for regio- and stereocontrol.
ACCOUNTS OF CHEMICAL RESEARCH
(2023)
Review
Chemistry, Organic
C. M. A. Afsina, Thaipparambil Aneeja, Mohan Neetha, Gopinathan Anilkumar
Summary: Copper-catalyzed organic reactions have attracted widespread attention due to the abundance and affordability of copper, as well as its low toxicity, eco-friendliness, sustainable nature, and versatility as a catalyst. These reactions are primarily used for the synthesis of biologically important nitrogen heterocycles, amines, amides, imines, and alkynes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yubei Dai, Fang Wang, Shengqing Zhu, Lingling Chu
Summary: We describe a novel Ni-catalyzed three-component cross-electrophile coupling reaction for the synthesis of fluoroalkyl-incorporated 1,3-dienes. This method exhibits a broad substrate scope and excellent selectivity, providing a new organometallic agent-free platform for the construction of fluoroalkyl-incorporated diene motifs.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Ariel L. Burgio, Nicklas W. Buchbinder, Webster L. Santos
Summary: A facile method for the synthesis of (Z)-1,3-enynes is achieved through sequential copper-catalyzed regio- and stereoselective borylation-protodeboronation of 1,3-diynes. Pinacolborane, copper(II) acetate, and Xantphos are utilized as the ligand to efficiently introduce hydrogen and Bpin in a cis fashion, followed by rapid hydrolysis with water. The reaction exhibits wide substrate scope and proceeds in a chemoselective manner.
Article
Chemistry, Physical
Kaituo Dong, Cristofer Pezzetta, Qiu-Cheng Chen, Alexander Kaushansky, Amedeo Agosti, Giacomo Bergamini, Robert Davidson, Lilac Amirav
Summary: Carbon-heteroatom cross-coupling reactions are important for industrial chemical processes, especially for the synthesis of pharmaceuticals, agrochemicals, and biologically active compounds. Photocatalyst/transition metal dual catalytic systems, using semiconductor nanoparticles as heterogeneous light sensitizers, offer advantages such as low-cost production, tunable photophysical properties, easy separation, high photostability, and recyclability. The combination of CdSe@CdS nanorod photocatalysts with a Ni complex catalyst enables efficient selective light-induced C-O cross-coupling reactions, achieving high yield and impressive turnover numbers.
Review
Chemistry, Multidisciplinary
Chandrasekar Praveen, Aurelien Dupeux, Veronique Michelet
Summary: The review discusses the catalytic activity of gold in functionalizing various C-H bonds with high selectivity, highlighting factors such as steric/electronic properties of C-H bonds, oxidation state of gold, and stereoelectronic capacity of coordinated ligands. It also reveals the potential applications of Au(I) and Au(III) species in regio- and site-selective activation of challenging C-H bonds, as well as the selective C-H bond activation with different heterocycles described in recent literature.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Physical
Vincent Davenel, Chloe Puteaux, Christian Nisole, Fabien Fontaine-Vive, Jean-Marie Fourquez, Veronique Michelet
Summary: Efficient routes to access functionalized bicyclo[3.2.1]oct-2-ene and bicyclo[3.3.1]nonadiene via indium-mediated cycloisomerization of 1,6-enynes have been developed. The optimization of an atom-economical catalytic process using InCl3 led to high yields of up to 99% for the preparation of functionalized bicyclic adducts. The choice between 5-exo and 6-endo pathways in the cyclization reaction was influenced by the substitution of the alkynyl moiety, with electron-withdrawing groups favoring the exo isomer.
Article
Chemistry, Inorganic & Nuclear
Idir Benaissa, Katarzyna Gajda, Laure Vendier, Noel Lugan, Anna Kajetanowicz, Karol Grela, Veronique Michelet, Vincent Cesar, Stephanie Bastin
Summary: The coordination chemistry of anionic NHC based on an IPy platform substituted at the CS position was studied with transition-metal centers, showing different coordination modes and reaction mechanisms. A gold(I) intermediate was also discovered during the process and structurally characterized. These complexes exhibited high activities and a large tolerance towards functional groups in the synthesis of carboxylic acid derivatives.
Article
Chemistry, Organic
Romain Laher, Emilie Gentilini, Christophe Marin, Veronique Michelet
Summary: The study focuses on the synthesis of original structures with bicyclic scaffolds for the fragrance industry and evaluates their potential organoleptic properties. NHC-gold-type catalysts show excellent activities in the synthesis of various bicyclic adducts. The research also compares the similarities and differences between starting ethers and their cycloisomerized bicyclic counterparts.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Vincenzo Marsicano, Antonio Arcadi, Veronique Michelet
Summary: In this study, alkyl- and aryl-substituted N-propargyl phthalimides were used as starting materials to selectively synthesize α-fluoro, β-phthalimido ketones, α,alpha-difluoro, β-phthalimido ketones, or β-phthalimido α-diketones through gold-catalyzed oxyfluorination/oxydifluorination or dioxygenation reactions. Key factors controlling product selectivity were identified, and the simultaneous assembly of the quinoxaline nucleus and removal of the phthalimido-protecting group were tested. Hypothetical reaction mechanisms for different reaction pathways were proposed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Elodie Louisy, Sandra Olivero, Veronique Michelet, Alice Mija
Summary: This study explores the potential of (R)-(+)-limonene, a major byproduct of the citrus industry, as a biobased thermoset precursor. The findings show that cis-LDO can be used to create highly promising biobased epoxy monomers for the production of high-performance thermoset materials.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Review
Chemistry, Organic
Aurelien Dupeux, Veronique Michelet
Summary: This article provides an overview of enantioselective strategies for the synthesis of oxazinoindoles and evaluates the bioactive properties of chiral oxazinoindoles.
SYNTHESIS-STUTTGART
(2023)
Review
Chemistry, Multidisciplinary
Elodie Louisy, Veronika Khodyrieva, Sandra Olivero, Veronique Michelet, Alice Mija
Summary: This paper presents a review of the applications of limonene oxide and dioxide as renewable raw materials for the development of biobased polymers. The polymerization techniques for limonene oxide and dioxide monomers are discussed.
Review
Chemistry, Multidisciplinary
Philippe Martinaux, Romain Laher, Christophe Marin, Veronique Michelet
Summary: This article introduces the application of transition metal-catalyzed cyclization reactions in fragrance synthesis, particularly in the synthesis of key skeletons. These reactions can improve atom economy and synthetic efficiency, providing new alternatives for the fragrance industry.
ISRAEL JOURNAL OF CHEMISTRY
(2023)
Review
Biochemistry & Molecular Biology
Romain Melot, Veronique Michelet
Summary: Coinage metals have shown great catalytic activity in organic transformation processes, making them the preferred choice for researchers. This review focuses on the recent development of coinage metal-catalyzed domino reactions using ortho-alkynylaryl and heteroaryl aldehydes and ketones, leading to functionalized heterocycles. The use of gold and silver chiral complexes as catalysts, as well as the preparation methods for chromenes and indoles, are discussed. The review also highlights the applications of copper and ruthenium in cyclization and asymmetric hydrogenation processes.
Article
Chemistry, Multidisciplinary
Kristina Plevova, Laura Juliana Prieto Pabon, Marc Gaysinski, Sophie Poulain-Martini, Veronique Michelet
Summary: Chiral Ag-atropisomeric ligand species were examined in solution at varying temperatures using P-31-NMR spectroscopy. The analysis of key parameters in Ag-BINAP complexes was conducted to understand their significance in an enantioselective transformation. An efficient silver-catalyzed intramolecular [4+2] cycloaddition of amide-1,6-enyne furnished an enantiomerically enriched tricyclic compound under mild reaction conditions using simple reagents.
Article
Chemistry, Applied
Romain Melot, Sandra Olivero, Veronique Michelet
Summary: A synthetic route for alkynylated saturated N-heterocycles was developed via a sequential combination of Shono oxidation and gold(I)-catalyzed alkynylation reaction. The electrochemical Shono oxidation enabled efficient access to various N,O-acetals through direct C-H bond functionalization of cyclic amines. The gold-catalyzed process allowed the introduction of aryl acetylene partners with different electron properties. Promising initial results on asymmetric version were obtained.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Alexis Truchon, Aurelien Dupeux, Sandra Olivero, Veronique Michelet
Summary: A gold-catalyzed orthogonal tandem reaction using HFIP as a Lewis acid has been developed to access carbocyclic ketone on naphthalene substrates. The yield of cyclic ketones ranged from 15% to 91% using a variety of acenaphthylene carbaldehydes. The mechanism involved a cyclization process followed by an [Au]-HFIP interaction for the final rearrangement. The gram-scale transformation and post-functionalization bromination were successfully carried out.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Alice Mija, Elodie Louisy, Sara Lachegur, Veronika Khodyrieva, Philippe Martinaux, Sandra Olivero, Veronique Michelet
Summary: This study valorizes the benign epoxidation of (R)-(+)-limonene to generate novel bio-resourced limonene dioxide monomers. The racemic limonene dioxide was cured with glutaric and dimethylglutaric anhydrides leading to thermosets with a high T-g and good mechanical properties.
Article
Chemistry, Organic
Maxime De Abreu, Yue Tang, Etienne Brachet, Mohamed Selkti, Veronique Michelet, Philippe Belmont
Summary: An efficient silver-catalyzed tandem reaction has been developed for the formation of 1,2-dihydroisoquinoline derivatives, providing a straightforward method to access highly functionalized multiheterocyclic scaffolds. This methodology offers a promising route for the synthesis and development of biologically relevant new heterocyclic pharmacophores, and allows for modifications at various sites of this pharmacophore.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Guojun Hu, Ziyue Deng, Yanwei Wang, Dan Yuan, Yong Zhang, Yingming Yao
Summary: A series of rare-earth metal complexes were synthesized and used as efficient initiators for the polymerization of trimethylene carbonate (TMC) and (L)-lactide ((L)-LA).
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Van Ha Nguyen, John H. K. Yip
Summary: In this study, eight PtII-azulene complexes were synthesized to investigate the effect of metalation on the electronic structures, spectroscopy, and luminescence of organic chromophores. The results showed that the attachment of Pt substituents to azulene affected the HOMOs, LUMOs, and luminescence properties. The study provides insights into the role of metalation in modifying the properties of organic chromophores.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Moon Kedia, Virender Singh, Bhaskaran Shankar, Malaichamy Sathiyendiran
Summary: This study synthesized two types of neutral binuclear metallocycles using a one-pot solvothermal method and characterized their structures. The analysis revealed that these complexes adopt a binuclear heteroleptic cyclic architecture and belong to phosphine oxide donor (P=O)-based supramolecular coordination cyclic complexes.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Radhey S. Srivastava
Summary: This study demonstrates the effectiveness of zero-valent elements as reductants for the deoxydehydration reaction of polyols catalyzed by ONO-pincer ligated molybdenum dioxo. The insolubility and easy separability of the reductants and their oxidized products during the reaction are emphasized. Additionally, the choice of ligand has an impact on the catalytic performance of the reaction.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Hao Zhou, Yajun Sun, Li Deng, Weiran Yang, Yuehui Li
Summary: Efficient Ru-catalyzed hydrogenation of aldehydes was achieved using carbazole-derived phosphine ligands, with the crucial role of N-H moiety in promoting the catalytic reaction. The method was successfully applied in the Co/Ru-catalyzed hydroformylation process, resulting in the production of long-chain alcohols with excellent yields.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Theodor Danescu, Alexandru Lupan, Radu Silaghi-Dumitrescu, R. Bruce King
Summary: The structures and energies of complexes containing (Me2C2N2P)2Ru2(CO)n and (Me2C2N2P)2Fe2(CO)n have been studied. Low-energy structures are characterized by the presence of bridging diazaphospholyl rings, while higher-energy structures involve different ligand structures.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Savannah C. Kapper, Aamani Ponnekanti, Jonas Schaab, Tian-yi Li, Christine L. Chung, Gael Ung, Peter I. Djurovich, Mark E. Thompson
Summary: Organometallic iridium complexes with two cyclometalated ligands and one bis-oxazoline derived ancillary ligand were studied. These complexes have emission spanning across the visible and near-ultraviolet region, with moderate to high photoluminescence quantum yields. The (ppy)2Ir(BOX-CN) complexes were resolved into Delta- and Lambda-diastereomers based on solubility differences.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Zahra Karimi Sangari, Hossein Naeimi
Summary: In this research, a nanostructured CoCuFe2O4 catalyst was prepared using a brief and useful synthetic strategy. This catalyst was used for synthesizing 1,2,4,5-tetrasubstituted imidazole derivatives under ultrasonic irradiation. The approach offers advantages such as high efficiency, short reaction times, simplicity of the reaction medium, accelerated reaction rates, and easier separation and purification of products.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Rukhsana Gul, Wajid Munir, Ebraheem Abdu Musad Saleh, Shaukat Shujah, Muhammad Sirajuddin, Saira Tabassum, Khalil Ur Rehman, Dilfaraz Khan, Sameerah I. Al-Saeedi, Ehab A. Abdelrahman
Summary: Two new Schiff base ligands were synthesized and used to form copper, nickel, and cobalt complexes. The synthesized compounds were characterized and screened for various biological activities. The metal complexes showed better activities in antibacterial, antifungal, antidiabetic, and antioxidant assays.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Review
Chemistry, Inorganic & Nuclear
Ahsan Nazir, Pengwei Huo, Ameena Tur Rasool
Summary: This review explores the potential of g-C3N4-based S-scheme heterojunctions in addressing environmental issues. It summarizes the mechanism and preparation techniques of S-scheme heterojunctions based on g-C3N4, and presents recent studies on their applications in pollutant removal, CO2 reduction, hydrogen production, and bacterial disinfection. The review concludes with an outlook on future challenges for g-C3N4-based S-scheme heterojunctions.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Francois Mazars, Koffi Senam Etse, Guillermo Zaragoza, Lionel Delaude
Summary: The activity of three Pd-PEPPSI catalyst precursors with N-heterocyclic carbene (NHC) ligands derived from caffeine and theophylline in Mizoroki-Heck reactions was tested. The results showed that the catalysts achieved high conversions and yields, especially in the presence of electron-withdrawing substituents.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
Article
Chemistry, Inorganic & Nuclear
Bo-Han Wu, Xue Zhou, Lin Liu, Zheng-Bo Han
Summary: Researching carbon dioxide removal from flue gas and natural gas is crucial. Metal-organic frameworks (MOFs) are commonly used in adsorption due to their high surface area, porosity, and chemical properties. An ultra-microporous MOF CPM-20(Co) with mixed ligand was synthesized using inexpensive ligands. The material exhibited high selectivities and low regenerative energy, making it a promising option for CO2 separation in industries.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2024)
