Article
Chemistry, Multidisciplinary
Nikki J. Bakas, Jeffrey D. Sears, William W. Brennessel, Michael L. Neidig
Summary: This study provides critical insights into the role of TMEDA as an additive in iron-catalyzed cross-coupling reactions. By using spectroscopic and crystallographic techniques, TMEDA-iron(II)-aryl intermediates are identified in the reaction cycle and it is found that their recombination with radicals leads to highly selective product formation. This research highlights the significance of TMEDA in modulating the selectivity and catalytic performance of organoiron species in cross-coupling reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Alexander Purtsas, Marco Rosenkranz, Evgenia Dmitrieva, Olga Kataeva, Hans-Joachim Knoelker
Summary: In this paper, the oxygenation and amination reactions of tertiary arylamines are described. The key steps of these coupling reactions involve iron-catalyzed oxidative C-O or C-N bond formation, which typically provide the desired products in high yields and with excellent regioselectivity. These transformations are carried out using hexadecafluorophthalocyanine-iron(II) (FePcF16) as catalyst, with the presence of an acid or base additive, and only require ambient air as the oxidant.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Nardana Sivendran, Nico Pirkl, Zhiyong Hu, Angelino Doppiu, Lukas J. Goossen
Summary: Halogen-bridged methylnaphthyl (MeNAP) palladium dimers, presented as versatile Pd precursors, demonstrate excellent catalytic performance by in situ conversion into well-defined monoligated complexes. They show benchmark activities in challenging reactions, enable record-setting yields, and can achieve previously elusive cross-couplings.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
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, 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)
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)
Review
Chemistry, Physical
Shasha Geng, Chaoqun Shi, Bohao Guo, Haoran Hou, Zhengli Liu, Zhang Feng
Summary: Transition-metal-catalyzed reductive cross-coupling reactions using diboron reagents as reductants have gained prominence due to their simplicity and good compatibility, offering advantages over conventional cross-coupling reactions.
Article
Chemistry, Multidisciplinary
Sara Lopez-Resano, Sara Martinez de Salinas, Felipe A. Garces-Pineda, Andrea Moneo-Corcuera, Jose Ramon Galan-Mascaros, Feliu Maseras, Monica H. Perez-Temprano
Summary: The potential access to Co-IV species to promote transformations challenging at Co-III in Cp*Co-catalyzed C-H functionalization reactions remains underexploited. We reveal the participation of Cp*Co-IV species in a Cp*Co-mediated C-S bond-reductive elimination through a combined experimental and computational strategy. These studies support the intermediacy of high-valent Cp*Co species in C-H functionalization reactions, particularly when involving nucleophilic coupling partners under oxidative conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Chao Jiang, Pinhong Chen, Guosheng Liu
Summary: In this study, a novel reaction technique combining photocatalysis and copper catalysis was developed for the radical decarboxylative C(sp(3))-C(sp(3)) cross-coupling of NHPI esters and cyclopropanols, leading to the efficient synthesis of ss-benzyl ketones. The terpyridin-4'-one ligand played a vital role in the reaction by facilitating the capture of benzylic radicals by alkyl-copper species generated through the copper-catalyzed ring-opening of cyclopropanols. The reaction exhibited broad substrate scope and wide functional group compatibility, providing a new approach for C(sp3)-C(sp3) bond formation.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Physical
Huan Zhou, Zhong-Liang Li, Qiang-Shuai Gu, Xin-Yuan Liu
Summary: Transition-metal-catalyzed asymmetric C-(sp(3))-C cross-coupling is an efficient method for the rapid synthesis of enantioenriched molecules. Chiral copper catalysts have been designed to promote a variety of asymmetric radical C(sp(3))-C cross-coupling reactions with high efficiency and enantioselectivity. The key to success lies in the design of chiral ligands to initiate the reaction and achieve enantiocontrol over the highly reactive prochiral alkyl radical species.
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)
Article
Chemistry, Physical
Dominik Birnthaler, Rok Narobe, Eliseo Lopez-Berguno, Christoph Haag, Burkhard Koenig
Summary: Ligand-to-metal charge transfer (LMCT) photo-catalysis enables the activation and utilization of halides and other heteroatoms in metal complexes. The application of bismuth LMCT in organic radical coupling reactions has been expanded, generating chlorine and carboxyl radicals in net-oxidative and redox-neutral photochemical reactions. The study reveals BiCl4- and BiCl52- as the catalytically active bismuth species under 385 nm irradiation, providing insight into the reactivity of the highly reactive bismuth(II) catalyst fragment through cyclic voltammetry and UV-vis studies.
Article
Chemistry, Multidisciplinary
Max J. Hulsey, Geng Sun, Philippe Sautet, Ning Yan
Summary: The article discusses the use of electrospray ionization mass spectrometry (ESI-MS) to study single-atom catalysts supported on polyoxometalates in catalytic reactions, revealing the composition of active sites and their evolution in the catalytic cycle.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Nanoscience & Nanotechnology
Yunjia Wei, Qi Hao, Xingce Fan, Mingze Li, Lei Yao, Guoqun Li, Xing Zhao, Hao Huang, Teng Qiu
Summary: This study proposes a new liquid-state surface-enhanced Raman scattering technique for managing and observing heterogeneous photocatalysis. By modulating the plasmonic hot carriers, the selection of reaction products is demonstrated, and various catalytic reaction mechanisms are investigated, revealing some new chemical reaction pathways.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Multidisciplinary
Jun-Jie Tian, Wei Sun, Rui-Rui Li, Gui-Xiu Tian, Xiao-Chen Wang
Summary: A borane/gold(I) co-catalytic system was designed and applied in C-H functionalization reactions and cycloaddition reactions between tertiary amines and alpha-alkynylenones, efficiently introducing a furan ring into the amine molecule.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Ines Manjon-Mata, M. Teresa Quiros, Elena Bunuel, Diego J. Cardenas
ADVANCED SYNTHESIS & CATALYSIS
(2020)
Article
Chemistry, Multidisciplinary
Maria Teresa Quiros, Enrique Gomez-Bengoa, Maria Paz Munoz
PURE AND APPLIED CHEMISTRY
(2020)
Article
Chemistry, Inorganic & Nuclear
Pablo Domingo-Legarda, Antonio Casado-Sanchez, Leyre Marzo, Jose Aleman, Silvia Cabrera
INORGANIC CHEMISTRY
(2020)
Article
Chemistry, Inorganic & Nuclear
Elena Cuellar, Alberto Diez-Varga, Tomas Torroba, Pablo Domingo-Legarda, Jose Aleman, Silvia Cabrera, Jose M. Martin-Alvarez, Daniel Miguel, Fernando Villafane
Summary: In this study, a series of new 1,2-azolylamidino complexes were synthesized and characterized using NMR, IR spectroscopy, and X-ray diffraction. Photophysical and electrochemical studies showed that these complexes exhibit good phosphorescence and reversible oxidation properties. Furthermore, the complexes were successfully used as catalysts in the photooxidation of different thioethers, with one of the complexes showing superior catalytic performance compared to a standard ruthenium complex.
INORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Michael T. Findlay, Pablo Domingo-Legarda, Gillian McArthur, Andy Yen, Igor Larrosa
Summary: This review focuses on the catalytic applications of cycloruthenated complexes in organic synthesis, with an emphasis on recent advancements in this field. Cycloruthenated complexes may exhibit enhanced catalytic activities compared to their non-cyclometallated analogues, or even possess entirely new reactivity, and they can also catalyze stereoselective reactions.
Article
Chemistry, Applied
Ines Manjon-Mata, M. Teresa Quiros, Elena Velasco-Juarez, Elena Bunuel, Diego J. Cardenas
Summary: A diastereoselective synthesis of borylated bicyclic 5-5 fused ring systems has been achieved through a domino Ni-catalyzed hydroborylative polycyclization of allenynes, providing two new C-C bonds and one C-B bond. The reaction is atom-economical, rapid, and tolerant to functional groups. The process involves oxidative cyclometallation, sigma-metathesis, and 1,2-insertion into the Ni-H bond, followed by reductive elimination.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Naishka E. Caldero-Rodriguez, Enrique M. Arpa, Diego J. Cardenas, Lara Martinez-Fernandez, Steffen Jockush, Sourav Kanti Seth, Ines Corral, Carlos E. Crespo-Hernandez
Summary: This study investigates the excited-state dynamics of 2-oxopurine riboside in aqueous solution and demonstrates its potential use as a dual fluorescent and photosensitizer analog for DNA and RNA research.
JOURNAL OF PHYSICAL CHEMISTRY B
(2022)
Review
Chemistry, Multidisciplinary
Jamie H. Docherty, Thomas M. Lister, Gillian Mcarthur, Michael T. Findlay, Pablo Domingo-Legarda, Jacob Kenyon, Shweta Choudhary, Igor Larrosa
Summary: Site-predictable and chemoselective C-H bond functionalization reactions are synthetically powerful strategies for the diversification of both feedstock and fine chemicals. However, challenges of regio- and chemoselectivity emerge when dealing with complex molecules with significant functional group density and diversity. Design and selection of reaction conditions and tolerant catalysts are critical for successful direct functionalization.
Article
Chemistry, Organic
M. Soledad Garre, Guillermo G. Otarola, Estibaliz Merino, David Sucunza, Enrique Aguilar, M. Teresa Quiros, Juan J. Vaquero, Patricia Garcia-Garcia
Summary: Cyclobutane-fused dihydropyridones can be synthesized efficiently via a completely endo-selective gold-catalyzed cyclization of alkynylcyclobutanes with an appended amide, under mild conditions. The observed selectivity, opposite to that observed for the cyclization of related alcohols and acids, is supported by DFT calculations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Carlos Lazaro-Milla, M. Teresa Quiros, Diego J. Cardenas, Pedro Almendros
Summary: The synthesis of skipped 1,4-enynes through functionalization of the cyclobutene core with alkynes has been achieved, indicating an unusual pathway of oxidative addition in tertiary iodoalkanes.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
M. Teresa Quiros, Daniel Collado-Sanz, Elena Bunuel, Diego J. Cardenas
Summary: The formation of catalytically active alkyl-Ni(i) complexes through alkyl ligand exchange proceeds easily through triplet states, involving inversion of the configuration at the transferred carbon.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Ana M. Martinez-Gualda, Pablo Domingo-Legarda, Thomas Rigotti, Sergio Diaz-Tendero, Alberto Fraile, Jose Aleman
Summary: The asymmetric synthesis of chiral polycyclic ethers is achieved through an intramolecular [2+2] photocycloaddition, utilizing a photocatalytically active iminium ion-based charge transfer complex under visible light irradiation. This method enables stereocontrolled [2+2] photocycloaddition, yielding tricyclic products with good enantiomeric ratios.
CHEMICAL COMMUNICATIONS
(2021)
