Article
Chemistry, Organic
Bryan C. Figula, D. Lucas Kane, Kaluvu Balaraman, Christian Wolf
Summary: Cross-coupling of alkyl fluorides and organocuprates is achieved via aluminum halide mediated C-F bond activation, leading to the formation of Csp2-Csp3 and Csp3-Csp3 bonds. The reaction exhibits mild conditions and effectively controls competing side reactions, resulting in high yields and good functional group tolerance.
Article
Chemistry, Inorganic & Nuclear
Francois Mazars, Guillermo Zaragoza, Lionel Delaude
Summary: The alkylation of caffeine with methyl iodide led to the synthesis of a new compound. Three complexes were obtained through multiple steps and were found to be highly active catalysts for the Suzuki-Miyaura cross-coupling reaction. The reaction showed high yields and could be carried out in a green solvent with low catalyst loading and in the presence of air.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Xuewen Guo, Jabor Rabeah, Ruixue Sun, Dengxu Wang, Esteban Mejia
Summary: A series of hybrid porous polymers (HPPs) based on polyhedral oligomeric silsesquioxane (POSS) were synthesized and successfully used as metal-free heterogeneous photocatalysts for cross-dehydrogenative coupling reactions, showing efficient catalytic performance under visible light. The novel catalysts can be easily recovered and reused, with mechanistic investigations revealing the oxidation-reduction process during photoexcitation.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Multidisciplinary
Sumanth Hegde, Aatika Nizam, Ajesh Vijayan, Ramesh B. Dateer, Suresh Babu Naidu Krishna
Summary: We have developed a magnetically recyclable palladium nanocatalyst capable of efficiently catalyzing the Suzuki-Miyaura cross-coupling reaction in an ethanol/water solution under ultrasonic conditions. The catalyst is compatible with various aryl halides and aryl boronic acids and exhibits excellent stability, low leaching, and heterogeneous nature.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Daniels Posevins, Aitor Bermejo-Lopez, Jan-E. Backvall
Summary: An iron-catalyzed cross-coupling reaction of propargyl ethers with Grignard reagents was disclosed, allowing for efficient chirality transfer and preparation of various fluoroalkyl allenes. Additionally, an iron-catalyzed cross-coupling of Grignard reagents with alpha-alkynyl oxetanes and tetrahydrofurans was demonstrated as a straightforward approach towards fully substituted beta- or gamma-allenols.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Multidisciplinary
Shelesh Krishna Saraswat, Ramanjaneyulu Seemaladinne, Media Noori Abdullah, Halim Zaini, Nabeel Ahmad, Nafis Ahmad, Esmail Vessally
Summary: Aryl fluorosulfates are versatile building blocks in organic synthesis and have gained increasing attention in SuFEx click chemistry. They can be easily prepared from phenols using low-cost sulfuryl fluoride as a sulfonyl fluoride provider. They have been used as less toxic and more atom economical alternatives to triflates in numerous cross-coupling reactions. This review summarizes the recent advances and developments in utilizing aryl fluorosulfates as electrophilic partners in cross-coupling reactions.
Article
Chemistry, Multidisciplinary
Giuseppe Dilauro, Francesco Messa, Fabio Bona, Serena Perrone, Antonio Salomone
Summary: A simple cobalt complex, Co(phen)Cl₂, has been found to be a highly efficient and cost-effective precatalyst for various cross-coupling reactions involving aromatic and aliphatic organoaluminum reagents with aryl, heteroaryl, and alkyl bromides. New C(sp²)-C(sp²) and C(sp²)-C(sp³) bonds can be formed in good to excellent yields and high chemoselectivity under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Shivhar B. Ambegave, Nitin T. Patil
Summary: This article provides an overview of the research progress in Au(I)/Au(III) catalysis, with a focus on cross-coupling reactions and 1,2-difunctionalization reactions of C-C multiple bonds. Understanding the reaction mechanisms is also highlighted as an important research direction.
Article
Chemistry, Inorganic & Nuclear
Carla Magallon, Oriol Planas, Steven Roldan-Gomez, Josep M. Luis, Anna Company, Xavi Ribas
Summary: This study investigates the intrinsic organometallic reactivity of iron within a tetradentate N3C macrocyclic ligand scaffold, leading to the stabilization of aryl-Fe species crucial in Fe-catalyzed cross-coupling and C-H functionalization processes. The synthesis of aryl-Fe-II complexes under light irradiation and moderate heating allowed for thorough spectroscopic characterization and investigation of their intrinsic reactivity.
Review
Chemistry, Applied
Suhelen Vasquez-Cespedes, Rick C. Betori, Megan A. Cismesia, Janelle K. Kirsch, Qiang Yang
Summary: Transition-metal-catalyzed cross-coupling reactions are crucial in organic chemistry, and the fine chemical industry has been exploring ways to reduce the amounts of transition metals used, with heterogeneous catalysis showing potential benefits. Despite the advantages of heterogeneous catalysis, its utilization in the fine chemical industry has decreased due to perceived difficulties in understanding and reproducibility. However, with the development of new supported metal catalysts, first-row transition metal catalysis, and continuous flow technology, there are tools available to overcome these challenges and promote the use of heterogeneous catalysis for cross-coupling reactions.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Multidisciplinary Sciences
Xu Luo, Dali Yang, Xiaoqian He, Shengchun Wang, Dongchao Zhang, Jiaxin Xu, Chih-Wen Pao, Jeng-Lung Chen, Jyh-Fu Lee, Hengjiang Cong, Yu Lan, Hesham Alhumade, Janine Cossy, Ruopeng Bai, Yi-Hung Chen, Hong Yi, Aiwen Lei
Summary: The authors report an on-cycle mechanism for CoCl2bpy2 catalyzed Negishi-type cross-coupling, elucidating the full catalytic cycle through multiple spectroscopic studies. Solvent and ligand were found to be crucial for generating catalytically active Co(I) species, with acetonitrile and bipyridine ligand resisting Co(I) disproportionation events. Combined investigations using Q-XAFS, EPR, IR, and DFT calculations provide comprehensive mechanistic insights into the structural information of the catalytic cobalt species and the entire Co(I)/Co(III) cycle. Additionally, the acetonitrile and bipyridine system can be extended to acylation, allylation, and benzylation reactions of aryl zinc reagents, demonstrating a broad substrate scope with a catalytic amount of Co salt. Overall, this work offers a fundamental mechanistic perspective for designing cobalt-catalyzed cross-coupling reactions.
NATURE COMMUNICATIONS
(2023)
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
P. S. Pharande, G. S. Rashinkar, D. M. Pore
Summary: A novel cellulose-supported Schiff base Pd(II) complex was successfully designed and synthesized, showing high catalytic activity and reusability in the Suzuki Miyaura cross-coupling of phenyl boronic acid and aryl halides. The method exhibited high TONs and TOFs, low catalyst loading, and the synthesis of novel biphenyl derivatives.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Review
Chemistry, Organic
Kinga Juhasz, Agnes Magyar, Zoltan Hell
Summary: This review summarizes the most important transition-metal-catalyzed cross-coupling reactions realized in the period from 2000 to 2020, covering a variety of important intermediates and catalysts.
SYNTHESIS-STUTTGART
(2021)
Review
Chemistry, Multidisciplinary
Myuto Kashihara, Yoshiaki Nakao
Summary: Cross-coupling reactions using nitroarenes as electrophiles have gained attention due to their ease of accessibility and potential advantages over haloarenes. Recent research has focused on developing new catalyst systems and reaction conditions to improve the efficiency and practicality of these reactions, with promising results in diversifying bond-forming reactions and reducing catalyst loading. Research in this field is expected to continue growing as the utility of nitroarenes in organic synthesis is reevaluated.
ACCOUNTS OF CHEMICAL RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Thomas M. Maier, Sebastian Sandl, Peter Melzl, Josef Zweck, Axel Jacobi von Wangelin, Robert Wolf
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Mikhail O. Konev, Luana Cardinale, Axel Jacobi von Wangelin
Article
Chemistry, Multidisciplinary
Michael Neumeier, Uttam Chakraborty, Dieter Schaarschmidt, Victor de la Pena O'Shea, Raul Perez-Ruiz, Axel Jacobi von Wangelin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Multidisciplinary
Luana Cardinale, Mikhail O. Konev, Axel Jacobi von Wangelin
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Editorial Material
Chemistry, Multidisciplinary
Thomas M. Maier, Sebastian Sandl, Peter Melzl, Josef Zweck, Axel Jacobi von Wangelin, Robert Wolf
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
Luana Cardinale, Michael Neumeier, Michal Majek, Axel Jacobi von Wangelin
Article
Chemistry, Multidisciplinary
Pradip Ghosh, Axel Jacobi von Wangelin
Summary: The reductive transformations of easily available oxidized matter play a crucial role in synthetic manipulation and chemical valorization. The use of liquid reducing agents and simple setups in catalytic hydrofunctionalization adds to its practicality. Metal-catalyzed hydroborations offer a productive platform for reductive valorizations of stable C=X electrophiles, as demonstrated in this study with the pre-catalyst Mn(hmds)(2) for the reduction of various functional groups under mild conditions, including successful depolymerizations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Pradip Ghosh, Roland Schoch, Matthias Bauer, Axel Jacobi von Wangelin
Summary: Metal-catalyzed C-H activation is an environmentally friendly and economically attractive synthetic strategy, which can reduce waste generation and reveal a tandem catalysis mechanism through a series of mechanistic studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Luana Cardinale, Mattis-Ole W. S. Schmotz, Mikhail O. Konev, Axel Jacobi von Wangelin
Summary: The study presents a straightforward protocol for the photocatalytic carbamoylation of imines using easily accessible and stable 4-amido Hantzsch ester derivatives as precursors to carbamoyl radicals. The reaction occurs under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and acid additives, with mechanistic studies suggesting a photoredox mechanism involving carbamoyl radicals.
Article
Chemistry, Inorganic & Nuclear
Andrey Fedulin, Sandeep K. Gupta, Isabelle Ruter, Franc Meyer, Axel Jacobi von Wangelin
Summary: The combination of pyridonate ligands with transition metal ions allows the synthesis of diverse coordination compounds. This study synthesized novel Fe5 and Fe4 clusters, with Fe5 cluster exhibiting a diamondoid structure and Fe4 cluster showing a butterfly motif. Magnetic tests revealed the rare single-molecule magnet behavior of Fe4 cluster.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ursula Rastetter, Axel Jacobi von Wangelin, Carmen Herrmann
Summary: To improve the catalytic activity of 3d transition metal catalysts, the use of redox-active ligands is promising. First-principles calculations, specifically density functional theory with a proper choice of exchange-correlation functional, are crucial for studying these ligands' influence on the electronic properties of metal complexes. Tests on a class of metal complexes showed that the spin-state energy splittings depend linearly on the amount of exact exchange included in the calculations. The sensitivity of the spin-state energetics to the exact exchange is surprisingly small, despite the significant impact of varying redox-activity on the electronic structure of the complexes.
JOURNAL OF COMPUTATIONAL CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sarah Kirchhecker, Ngoc Nguyen, Stefan Reichert, Karola Luetzow, Paul Eselem S. Bungu, Axel Jacobi von Wangelin, Sebastian Sandl, Axel T. Neffe
Summary: The combination of inexpensive Fe(ii) acetate with low molecular weight aliphatic carboxamides in situ generates an effective catalyst system for the ring opening polymerisation of lactones. PLLAs with high molar masses, narrow dispersity, and without racemisation were successfully produced. Furthermore, the synthesis of PLLA-PCL block copolymers with low randomness was achieved. This catalyst mixture has the potential to be used in polymers with biomedical applications.
Review
Chemistry, Physical
Andrey Fedulin, Axel Jacobi von Wangelin
Summary: Aminoalcohols are a readily available, highly diverse, and inexpensive class of ligands. Among them, 2-pyridonates exhibit particularly intriguing stereoelectronic features and have been applied to various coordination chemistry reactions. Transition metal complexes with pyridonate ligands have been developed for powerful catalytic transformations.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Review
Chemistry, Physical
Dominik Gaertner, Sebastian Sandl, Axel Jacobi von Wangelin
CATALYSIS SCIENCE & TECHNOLOGY
(2020)
Article
Chemistry, Multidisciplinary
Patrick Bayer, Axel Jacobi von Wangelin
