Review
Chemistry, Multidisciplinary
Hayato Fujimoto, Kosuke Yasu, Mamoru Tobisu
Summary: This report discusses recent studies on catalytic transformations involving a non-classical mode of molecular activation by tertiary phosphines and N-heterocyclic carbenes (NHCs). The results show that by designing specific catalytic protocols, synthetic transformations that are otherwise unattainable can be achieved, including intermolecular carbofluorination of alkynes and hydroalkenylation of enol ethers. The use of imidazolium-based NHCs was explored for nucleophilic aromatic substitution reactions as well as nucleophilic activation of styrene derivatives, generating non-stabilized vinyl anion equivalents.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2023)
Article
Chemistry, Multidisciplinary
Xiaohua Hou, Xiaojian Chen, Xiang Gao, Lei Xu, Hui Zou, Li Zhou, Zong-Quan Wu
Summary: The binuclear vanadium alkylidene showed higher activity in ROMP of norbornene, leading to the formation of cyclic polymers. The size of the polymer ring could be adjusted by the vanadium catalyst structure and polymerization temperature. Similar results were also observed in the ROMP of cyclopentene.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Stefan Czarnocki, Louis Monsigny, Michal Sienkiewicz, Anna Kajetanowicz, Karol Grela
Summary: A modular and flexible strategy for synthesizing N-heterocyclic carbene (NHC) ligands bearing Bronsted base tags has been proposed and used to prepare two tagged NHC ligands with different acid residues. These tagged NHC ligands serve as an attractive starting point for the synthesis of olefin metathesis ruthenium catalysts with non-dissociating ligands. The impact of the Bronsted base tags on the activity of the obtained olefin metathesis catalysts has been investigated.
Review
Chemistry, Multidisciplinary
Antonio Del Vecchio, Harry R. Smallman, Jennifer Morvan, Tom McBride, Duncan L. Browne, Marc Mauduit
Summary: This article introduces the versatility of olefin metathesis and its successful applications in natural product synthesis and the valorization of renewable feedstocks. In addition, flow chemistry has gained significant interest as a valuable alternative to traditional batch chemistry and has paved the way for new transformations. The article highlights the promising application of continuous-flow methods in olefin metathesis, addressing typical issues such as undesired self-reactions and ethylene-mediated catalyst deactivation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Mingxin Liu, Nguyen Le, Christopher Uyeda
Summary: Nickel catalysts promote nucleophilic cyclopropanation reactions using CH2Cl2 as a methylene source and Mn as a stoichiometric reductant. The substrate scope includes a broad range of alkenes bearing electron-withdrawing substituents, and enantioselective cyclopropanations have been developed using chiral PyBox ligands. Mechanistic studies suggest the intermediacy of a (PyBox)Ni=CH2 species and DFT models provide a rationale for the nucleophilic character of the nickel carbene and the sense of enantioinduction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Augustin Nouaille, Xavier Pannecoucke, Thomas Poisson, Samuel Couve-Bonnaire
Summary: This study presents an efficient ruthenium-catalyzed CM reaction method, successfully allowing various alkenes to react with methyl 2-fluoroacrylate to obtain trisubstituted fluoroalkenes for the first time. Additionally, an unprecedented TON value for the CM reaction involving fluoroalkenes was achieved, demonstrating good tolerance and effectiveness with a wide range of olefin partners.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Jennifer Morvan, Marc Mauduit, Guy Bertrand, Rodolphe Jazzar
Summary: The discovery of cyclic (alkyl)(amino) carbenes (CAACs) in 2005 revolutionized the field of ruthenium olefin metathesis by providing stronger metal-carbene bonds and increased catalytic activity, as demonstrated in patents.
Review
Chemistry, Physical
Dominique Matt, Jack Harrowfield
Summary: Tertiary phosphines and other P(III)-derivatives play a crucial role in homogeneous catalysis, especially compounds with cavity-shaped subunits. This review illustrates the utility of covalently-constructed phosphines that incorporate a cavity and highlights future directions in ligand design.
Article
Chemistry, Inorganic & Nuclear
Michal Patrzalek, Adam Zielinski, George Pasparakis, Maria Vamvakaki, Anna Ruszczynska, Ewa Bulska, Anna Kajetanowicz, Karol Grela
Summary: This study investigates purification methods for aqueous media olefin metathesis reactions to address the challenge of removing the catalyst from the reaction products. The addition of thiocyanate ions successfully removes the catalyst from water, but the methodology does not provide satisfactory results for reactions performed in water/alcohol mixtures.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Raphael J. Zachmann, Alois Fuerstner
Summary: The newly discovered light-driven gem hydrogenation of alkynes provides a safe and versatile approach to synthesizing Grubbs-type ruthenium carbene complexes, using a triple bond as the carbene source without needing sacrificial phosphines.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Inorganic & Nuclear
Natsuki Yabune, Hiroshi Nakajima, Takanori Nishioka
Summary: The use of alkylene-bridged bis-N-heterocyclic carbene ligands enhances the reactivity of the Pt3S2 core in a triplatinum complex. Despite the potential reaction between an Ag(i) ion and the Pt-Pt bond, steric hindrance results in coordination of one sulfide ligand to the Ag(i) ion.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Multidisciplinary
Miquel Navarro, Markus Holzapfel, Jesus Campos
Summary: A cavity-shaped gold(I) complex derived from a bulky tri-(ortho-biaryl)-phosphine ligand exhibits preferred selectivity towards terminal functionalities in the gold(I)-catalysed hydration of alkynes under mild heating, thanks to a well-defined pocket as the catalytic active site. This selectivity differs from other gold(I) complexes with bulky phosphine ligands, which show reduced selectivity or similar behavior towards both internal and terminal alkynes. We also explore the potential of gold(III) derivatives for the same catalytic process.
Article
Chemistry, Multidisciplinary
Arnab K. Maity, Annah E. Kalb, Matthias Zeller, Christopher Uyeda
Summary: (NDI)Ni-2 catalysts promote cyclopropanation reactions of 1,3-dienes by coupling with (Me3Si)CHN2. Mechanistic studies and DFT models suggest an alternative reaction mechanism involving Ni-2 mediated coupling and N-2 extrusion for generating cyclopropane products, explaining the experimental observations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Wioletta Kosnik, Dawid Lichosyt, Marcin Sniezek, Angelika Janaszkiewicz, Krzysztof Wozniak, Maura Malinska, Bartosz Trzaskowski, Anna Kajetanowicz, Karol Grela
Summary: The formation of sterically hindered C-C double bonds through catalytic olefin metathesis is a challenging task for Ru catalysts. To overcome this limitation, a new NHC ligand was designed, which reduced the susceptibility of small-size NHC catalysts to decomposition. The resulting isomeric complexes exhibited similar high thermodynamic stability but different application profiles in catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Changpeng Chen, Feng-Shou Liu, Michal Szostak
Summary: The discovery of NHCs as ancillary ligands has greatly improved catalytic processes, with BIAN-NHC ligands in particular showing enhanced reactivity due to combinations of electronic and steric properties. The development of BIAN-NHC ligands has led to major advancements in catalysis and offers a practical alternative to classical NHCs.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Anupam Jana, Karol Grela
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Adrian Sytniczuk, Gwenael Forcher, Douglas B. Grotjahn, Karol Grela
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Phillip I. Jolly, Anna Marczyk, Pawel Malecki, Osman Ablialimov, Damian Trzybinski, Krzysztof Wozniak, Silvio Osella, Bartosz Trzaskowski, Karol Grela
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Manfred Karras, Michal Dabrowski, Radek Pohl, Jiri Rybacek, Jaroslav Vacek, Lucie Bednarova, Karol Grela, Ivo Stary, Irena G. Stara, Bernd Schmidt
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Adrian Sytniczuk, Agnieszka Leszczynska, Anna Kajetanowicz, Karol Grela
Article
Chemistry, Inorganic & Nuclear
Adam Zielinski, Grzegorz Szczepaniak, Roman Gajda, Krzysztof Wozniak, Bartosz Trzaskowski, Dragoslav Vidovic, Anna Kajetanowicz, Karol Grela
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2018)
Article
Chemistry, Inorganic & Nuclear
Anna Gawin, Eva Pump, Christian Slugovc, Anna Kajetanowicz, Karol Grela
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Niyaz Z. Yagafarov, Karim M. Muratov, Klim Biriukov, Dmitry L. Usanov, Olga Chusova, Dmitry S. Perekalin, Denis Chusov
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Grzegorz Szczepaniak, Anna Ruszczynska, Krzysztof Kosinski, Ewa Bulska, Karol Grela
Article
Chemistry, Physical
Anna Gawin, Pawel Malecki, Maciej Dranka, Janusz Zachara, Magdalena Skompska, Anna Kajetanowicz, Karol Grela
JOURNAL OF CATALYSIS
(2018)
Article
Chemistry, Inorganic & Nuclear
Sofiya A. Runikhina, Mikhail A. Arsenov, Vladimir B. Kharitonov, Elizaveta R. Sovdagarova, Olga Chusova, Yulia V. Nelyubina, Gleb L. Denisov, Dmitry L. Usanov, Denis Chusov, Dmitry A. Loginov
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Dmitry L. Usanov, Alix Chan, Juan Pablo Maianti, David R. Liu
Review
Chemistry, Organic
Nirmalya Mukherjee, Sebastian Planer, Karol Grela
ORGANIC CHEMISTRY FRONTIERS
(2018)
Article
Chemistry, Organic
Oleg I. Afanasyev, Alexander Zarochintsev, Tatiana Petrushina, Anastasia Cherkasova, Gleb Denisov, Ilia Cherkashchenko, Olga Chusova, Oh Jinho, Chun Man-Seog, Dmitry L. Usanov, Sergei E. Semenov, Denis Chusov
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Editorial Material
Chemistry, Organic
Karol Grela, Anna Kajetanowicz
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2019)