Article
Chemistry, Applied
Tobias Wagener, Marco Pierau, Arne Heusler, Frank Glorius
Summary: In this study, a one-pot protocol for the synthesis of octahydroindoles, decahydroquinolines, and octahydroindolizines through a cascade reaction is presented.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Yuya Kaieda, Kosuke Yamamoto, Masami Kuriyama, Osamu Onomura
Summary: A rhodium-catalyzed reaction has been developed to convert N-sulfonyl-1,2,3-triazoles and carboxylic esters into 2,5-disubstituted oxazole derivatives under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Xinxin Tang, Raj K. Tak, Hidetoshi Noda, Masakatsu Shibasaki
Summary: We report the stereoselective synthesis of remotely decorated, trisubstituted beta-prolines via Rh-catalyzed C-H amination. The method works well in the presence of various functionalities, with carboxylic acids in the products serving as gateways for diverse downstream transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Sebastian Mummel, Felix Lederle, Eike G. Huebner, Jan C. Namyslo, Martin Nieger, Andreas Schmidt
Summary: Sydnone methides are rare compounds that can form pi-electron rich anionic N-heterocyclic carbenes and coordinate with various metals, while also undergoing C-C coupling reactions under specific catalysts. Studies have determined their electronic properties and NMR spectra.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Veronica Papa, Johannes Fessler, Francesco Zaccaria, Julien Hervochon, Phong Dam, Christoph Kubis, Anke Spannenberg, Zhihong Wei, Haijun Jiao, Cristiano Zuccaccia, Alceo Macchioni, Kathrin Junge, Matthias Beller
Summary: In this study, several imidazolylphosphine pincer ligands and corresponding Mn complexes were synthesized, characterized, and studied in depth using experimental and theoretical investigations. The complexes showed good to excellent performance in various hydrogenation reactions, particularly in the reduction of N-heterocycles. Spectroscopic studies provided evidence for a classical metal-ligand cooperative mechanism and identified amido and hydrido species.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Applied
Yasuaki Fukazawa, Vladimir Yu. Vaganov, Julia V. Burykina, Artem N. Fakhrutdinov, Ruslan I. Safiullin, Felix Plasser, Aleksandr E. Rubtsov, Valentine P. Ananikov, Andrei V. Malkov
Summary: The mechanism of metal-catalyzed asymmetric alkylation of indoles remains uncertain. In this study, the authors investigate the mechanism from both molecular and nano-level perspectives, revealing the role of water and catalyst precursor on reaction selectivity and performance.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Zhen-Hua Wang, Ji-Hong Liu, Yan-Ping Zhang, Jian-Qiang Zhao, Yong You, Ming-Qiang Zhou, Wen-Yong Han, Wei-Cheng Yuan
Summary: In this study, the enantioselective desymmetrization of N-arylmaleimides was achieved using a Cu(OTf)(2)/chiral ferrocenyl P,N-ligand complex as a catalyst, through the asymmetric 1,3-dipolar cycloaddition reaction of N-2,2,2-trifluoroethylisatin ketimines. A series of structurally diverse F3C-containing octahydropyrrolo[3,4-c]pyrroles, bearing four contiguous carbon stereocenters and one stereogenic chiral C-N axial bond, were obtained with excellent results (<= 99% yield, >20:1 dr, and 99% ee).
Article
Multidisciplinary Sciences
Yu Chang, Chuandong Xie, Hong Liu, Shengli Huang, Pengfei Wang, Wenling Qin, Hailong Yan
Summary: 1,2-Azoles are privileged structures in many natural products and drugs. The authors report an atroposelective synthesis of two types of axially chiral 1,2-azoles through vinylidene ortho-quinone methide intermediates.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Jingya Yang, Wentong Ma, Shengyu Wang, Jiangjiang Li, Hongyan Zhou
Summary: A visible-light-mediated cycloaddition method for the synthesis of 1,2,4-triazolidines has been developed. Using the organic dye rose bengal as a photocatalyst and alkyl tertiary amines as precursors, the reaction proceeded smoothly under visible light irradiation at room temperature, yielding the desired products with high yields.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Applied
Atsushi Umehara, Soma Shimizu, Makoto Sasaki
Summary: This report presents a general method for the direct N-acylation of N-heterocycles using the DMAPO/Boc(2)O system. This one-pot method allows for the synthesis of bulky N-acyl heterocycles from less nucleophilic N-heterocycles and sterically hindered carboxylic acids. The protocol has also been successfully applied to the one-pot N-acylation of 7-azaindoles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Inorganic & Nuclear
Robin Guthardt, Johanna Mellin, Clemens Bruhn, Ulrich Siemeling
Summary: In this study, new ferrocene derivatives and complexes were synthesized and structurally characterized by single-crystal X-ray diffraction. Compounds 1 and 2 represent a new class of ferrocene-based bidentate ligands. Electrochemical investigation revealed the presence of three redox-active moieties in these compounds.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Adam J. Zoll, Jenna C. Molas, Brandon Q. Mercado, Jonathan A. Ellman
Summary: A multicomponent annulation that proceeds by imine directed Cp*Rh-III-catalyzed N-H functionalization has been developed, which provides piperazinones with a range of functionality. This is the first example of transition metal-catalyzed multicomponent N-H functionalization. Mechanistic studies support the proposed mechanism and the efficient transformation of the piperazinone products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Josh Abbenseth, Oliver P. E. Townrow, Jose M. Goicoechea
Summary: A geometrically constrained phosphine bearing a tridentate NNS pincer ligand has been successfully used to reversibly activate ammonia through N-H bond scission upon mild heating in solution, as demonstrated through experimental and theoretical studies. The geometric constraint also leads to the formation of cooperative addition products, and the thermodynamics of these transformations are substrate-dependent.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tsukasa Tawatari, Ritsuki Kato, Riku Kudo, Kiyosei Takasu, Hiroshi Takikawa
Summary: In this study, we report on the intramolecular (3+2) cycloaddition reactions between ynamides and benzyne. These reactions involve the formation of two bonds and are facilitated by using benzyne precursors containing a chlorosilyl group. The intermediate indolium ylide in these reactions exhibits both nucleophilic and electrophilic properties at its C2 atom.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jacob C. Hood, Maksim V. Anokhin, Douglas A. Klumpp
Summary: N-Heterocyclic alcohols have been proven to be excellent substrates for superacid-promoted Friedel-Crafts reactions. The ionization of N-heterocyclic alcohols produces reactive, dicationic intermediates, leading to good to excellent yields of arylation products.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Luong Phong Ho, Angelika Neitzel, Thomas Bannenberg, Matthias Tamm
Summary: In this study, a series of sulfur and selenium compounds with different metal complexes were synthesized through experimental and computational methods, revealing their bonding situation and properties.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Jayeeta Bhattacharjee, Dirk Bockfeld, Matthias Tamm
Summary: The reactions of N-heterocyclic carbene-phosphinidene adducts with dinuclear ruthenium and osmium complexes resulted in the formation of half-sandwich complexes with different geometries. The ruthenium complex showed high activity in the hydroboration of various substrates under mild reaction conditions. Preliminary mechanistic and kinetic studies suggested the formation of a monohydride complex as the catalytically active species.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Luong Phong Ho, Matthias Tamm
Summary: This article provides a brief overview of the design and preparation of N-heterocyclic carbenes carrying weakly coordinating anions, and summarizes numerous transition metal and main group element complexes isolated in the past decade.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Inorganic & Nuclear
Luong Phong Ho, Matthias Tamm
Summary: In this study, chalcogen-pnictogen dihalide complexes with anionic N-heterocyclic carbene ligands containing a weakly coordinating borate moiety were isolated and characterized.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Inorganic & Nuclear
Marius Peters, Dirk Bockfeld, Matthias Tamm
Summary: This study reports the synthesis of novel iridium complexes and their application in catalytic reactions. Neutral and cationic complexes were obtained through reactions with specific ligands, and these complexes exhibited high activity in catalytic reactions of aromatic substrates.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Daniel Becker, Dirk Bockfeld, Matthias Tamm
Summary: In this study, two complexes were obtained by reacting the bidentate [P,N] ligand with [Ir(COD)Cl] and adding different ligands, and further reaction yielded a diiridium tetrahydride. Crystal structure analysis of the three complexes revealed that the position of the hydrogen atoms in one of the complexes could be refined freely. Since the first complex is a validated catalyst, the performance of the two complexes in deuterium labeling reactions was compared.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Maxim Khononov, Heng Liu, Natalia Fridman, Matthias Tamm, Moris S. Eisen
Summary: Mono-substituted imidazolin(X)-2-iminato hafnium(IV) complexes were synthesized and found to be active catalysts for the ring-opening polymerization of epsilon-caprolactone.
Article
Chemistry, Inorganic & Nuclear
Lukas Koerner, Linpan Yang, Dirk Bockfeld, Matthias Tamm
Summary: In this study, a series of 1,1-enediamines were synthesized and transformed into corresponding complexes with gold, palladium, and boron ligands. The new complexes were fully characterized by NMR spectroscopy and X-ray diffraction analysis, revealing their similarities to N-heterocyclic olefins in terms of structural features.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Adinarayana Doddi, Marius Peters, Dirk Bockfeld, Matthias Tamm
Summary: The reaction of N-heterocyclic carbene-parent phosphinidene adducts with copper(I) or silver(I) chloride resulted in the formation of monometallic complexes. Single-crystal X-ray diffraction analysis revealed that the (IMes)PH ligand tends to form polynuclear structures, while the larger (IDipp)PH ligand forms mononuclear complexes. The bimetallic complexes could not be isolated in pure form due to their instability in solution.
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE
(2023)
Article
Chemistry, Physical
Lars Denker, Daniela Wullschlaeger, Juan Pablo Martinez, Stanislaw Swierczewski, Bartosz Trzaskowski, Matthias Tamm, Rene Frank
Summary: The amino imidazolin-2-imine ligand [HAmIm, 1,2(DippNH)-C6H4-N=C(NiPrCMe)(2)] has been found to be a highly efficient (pre)catalyst in H/D exchange reactions and hydrosilylation reactions with deuterium and primary to tertiary silanes. The study includes control experiments and theoretical calculations to explore the possible reaction mechanisms.
Article
Chemistry, Physical
Hemanta Deka, Natalia Fridman, Marvin Koneczny, Matthias Tamm, Moris S. Eisen
Summary: A series of thorium and uranium complexes decorated with unsymmetrical imidazolin-2-iminato ligands were synthesized and found to be effective as catalysts for the transfer hydrogenation of aldehydes and ketones with alcohols. The reaction showed good selectivity and tolerance towards various functional groups, including those prone to reduction. The neutral imine ligand was coordinated in the active catalyst along with the alkoxo group.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Inorganic & Nuclear
Rong Sun, Chen Wang, Bing-Wu Wang, Zhe-Ming Wang, Yao-Feng Chen, Matthias Tamm, Song Gao
Summary: Lanthanide-based single-molecule magnets (Ln-SMMs) have shown the highest effective barrier and blocking temperature among all SMMs. Different strategies, including reducing coordination number and weakening molecular vibrations, have been proposed to construct high-performance SMMs. However, the synthesis of low-coordinate Ln(iii) complexes remains challenging due to their large ionic radius and ionic nature.
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Lilian Sophie Szych, Karsten Paul Ludtke, Alexander Villinger, Dirk Bockfeld, Matthias Tamm, Axel Schulz
Summary: The synthesis of sterically demanding 2,6-bis-(2,4,6-trimethylphenyl)-phenyl (Ter)-stabilized and H-substituted diphosphanes via conversion of phosphide with secondary chlorophosphanes is described. The resulting potassium phosphinophosphides can be further functionalized and selectively used to synthesize Si-substituted diphosphanes or triphosphanes.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Adinarayana Doddi, Thomas Bannenberg, Dirk Bockfeld, Matthias Tamm
Summary: Half-sandwich iridium complexes of [(eta(5)-C5Me5){(NHC)E}IrCl] (E=P, As) were synthesized using N-heterocyclic carbene (NHC) adducts of (IDipp)ESiMe3 and (IMes)ESiMe3 with [(eta(5)-C5Me5)IrCl2](2). The X-ray diffraction analysis of [(eta(5)-C5Me5){(IDipp)As}IrCl] confirmed its molecular structure, revealing the first structurally authenticated NHC-arsinidenide complex with a shorter Ir-As bond length and significant metal-arsenic pi-interaction, as supported by theoretical calculations.
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE
(2023)
Article
Chemistry, Inorganic & Nuclear
Marvin Koneczny, Arife Busra Erol, Marc Mauduit, Moris S. Eisen, Matthias Tamm
Summary: A series of unsymmetrical N-heterocyclic carbene imidazoline and imidazolin-2-imine ligands were synthesized and their metal complexes were characterized by X-ray diffraction analysis, except for one compound.
DALTON TRANSACTIONS
(2022)