Article
Chemistry, Physical
Abbas Akdeniz, Nevin Turan
Summary: Cross-coupling reactions are powerful tools for carbon-carbon bond formation in organic synthesis. Palladium-catalyzed cross-coupling reactions have attracted significant attention. Two new Schiff base-Pd(II) complexes were synthesized and characterized. The complexes were applied in Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, showing high yields. Electron-donating and electron-withdrawing substituents on aryl halides can produce coupling products in perfect yield in the presence of these complexes.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Multidisciplinary
Hamed M. Alshammari, Obaid F. Aldosari, Mohammad Hayal Alotaibi, Raja L. Alotaibi, Mosaed S. Alhumaimess, Moataz H. Morad, Syed Farooq Adil, Mohammed Rafi Shaik, Mohammad Shahidul Islam, Mujeeb Khan, Abdulrahman Alwarthan
Summary: Pd/C catalysts on activated carbon with varying palladium content showed high catalytic activity for Suzuki-Miyaura coupling reactions and Mizoroki-Heck cross-coupling reactions. The catalyst with 3% Pd/C demonstrated better efficiency and reusability compared to other synthesized catalysts, indicating the significance of high 'Pd' content and uniform impregnation on the catalyst activity.
APPLIED SCIENCES-BASEL
(2021)
Article
Materials Science, Paper & Wood
Arnet Maria Antony, Masira Imtiyaz Chamanmalik, Vishal Kandathil, Harini G. Sampatkumar, B. S. Sasidhar, C. V. Yelamaggad, Siddappa A. Patil
Summary: A new N-heterocyclic carbene-palladium(II) complex grafted on cellulose was synthesized as a heterogeneous catalyst. The structure, morphology, thermal stability and chemical composition of the catalyst were confirmed by various analytical techniques. The catalyst exhibited excellent catalytic ability in Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with good tolerance to various functional groups and easy recovery by filtration.
Article
Chemistry, Multidisciplinary
Nadiya Koukabi, Maryam Arghan
Summary: In this study, magnetic starch from apple seeds was proposed as a perfect substrate material for catalysis. The fabricated catalyst, Fe3O4@starch-Co(II), exhibited high efficiency and eco-friendly properties. The catalyst showed promising potential as a replacement for toxic palladium-based catalysts in Mizoroki-Heck and Suzuki-Miyaura reactions, and it could be easily recovered and reused multiple times due to its magnetic properties.
RESEARCH ON CHEMICAL INTERMEDIATES
(2022)
Article
Chemistry, Applied
Hassan Eslahi, Ali Reza Sardarian, Mohsen Esmaeilpour
Summary: A novel magnetic and heterogeneous palladium-based catalyst was synthesized and fully characterized, showing high activity in cross-coupling reactions. The catalyst, stabilized by glucosamine, demonstrated excellent recyclability for consecutive reaction cycles without significant reduction in catalytic activity.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Review
Chemistry, Physical
Gianluigi Albano, Antonella Petri, Laura Antonella Aronica
Summary: In recent years, there has been extensive research on immobilizing palladium nanoparticles on solid supports for the preparation of active and stable catalytic systems. Compared to inorganic materials, naturally occurring organic solids are more cost-effective and readily available. This review focuses on the application of metal catalysts supported by natural biomaterials in C-C bond formation reactions, specifically Mizoroki-Heck, Suzuki-Miyaura, and Sonogashira reactions. Different types of organic matrices, such as cellulose, starch, pectin, agarose, chitosan, as well as proteins and enzymes, are discussed, highlighting the heterogeneous nature and recyclability of each catalyst.
Article
Chemistry, Physical
Masoumeh Beiranvand, Davood Habibi
Summary: In this study, the mesoporous silica SBA-15 (SBA) was modified by a tetra-urea (TU) ligand to prepare the SBA@TU@Pd(0) nano-structured reduced catalyst. The catalytic activity of SBA@TU@Pd(0) was successfully studied in the Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions, showing short reaction times and high yields. The non-reduced nano-catalyst SBA@TU@Pd(II) also exhibited similar reaction yields but longer reaction times.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Physical
Asanda C. Matsheku, Richard Tia, Munaka C. Maumela, Banothile C. E. Makhubela
Summary: Carbon-carbon cross-coupling reactions are crucial for synthesizing various compounds, and newly prepared ferrocenylimine ligands showed promising catalytic activity in Mizoroki-Heck and Suzuki-Miyaura reactions.
Article
Materials Science, Multidisciplinary
Khaoula Oudghiri, Lahoucine Bahsis, Said Eddarir, Hafid Anane, Moha Taourirte
Summary: A green protocol for the in situ synthesis of Pd nanoparticles on chitosan beads (Pd NPs-CS) without toxic reducing agents was reported. The Pd nanoparticles catalyst was prepared by a simple coordination reaction between chitosan beads and palladium ions. The Pd NPs-CS catalyst showed high catalytic activity and selectivity in Suzuki-Miyaura cross-coupling reaction and Heck reaction, with the bead form of the catalyst easily separated from the reaction mixture.
Article
Chemistry, Physical
Arif Naim Rosnizam, Muhamad Azwan Hamali, Anis Low Muhammad Low, El Hassane Anouar, Hany M. Youssef, Hadariah Bahron, Amalina Mohd Tajuddin
Summary: Two N,O-bidentate ligands and their Pd(II) complexes were synthesized and characterized. The crystal structure analysis revealed a square planar geometry with bis-bidentate coordination. The intercontact between complex units was analyzed using Hirshfeld surface analysis and electrostatic potentials maps. The antibacterial activity and catalytic efficiency of the compounds were evaluated.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Polymer Science
Ameneh Ahmadi, Tahereh Sedaghat, Roya Azadi
Summary: In this study, a Palladium-based magnetic nanocomposite was synthesized and utilized as a catalyst for Suzuki coupling and Heck-Mizoroki coupling reactions, demonstrating efficient catalytic activity and recyclability.
JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS
(2021)
Article
Chemistry, Applied
Mingyang Gao, Jiamin Wang, Weixiang Shang, Yuchao Chai, Weili Dai, Guangjun Wu, Naijia Guan, Landong Li
Summary: Suzuki-Miyaura cross-coupling reaction is a powerful method to construct carbon-carbon bonds and is widely used in the synthesis of functional organic compounds. In this study, zeolite-encased Pd particles (Pd@MFI) were successfully prepared and investigated as promising heterogeneous catalysts for the Suzuki-Miyaura cross-coupling reaction. The Pd@MFI catalysts showed high activity, with dispersed Pd particles efficiently stabilized within the MFI zeolite matrix. The presence of basic sites adjacent to Pd sites was crucial for achieving high catalytic activity.
Article
Chemistry, Multidisciplinary
Mahdieh Ghabdian, Mohammad Ali Nasseri, Ali Allahresani, Alireza Motavallizadehkakhky
Summary: A Pd(II) Schiff base complex supported on graphene oxide nanosheets (Pd(II) salen@CPGO) has been synthesized and characterized, showing excellent catalytic efficiency for Suzuki-Miyaura and Heck-Mizoroki coupling reactions. The solid sheet-supported Pd catalyst can be easily separated and recycled multiple times without significant loss of catalytic activity, making it a promising system for heterogeneous catalytic reactions.
RESEARCH ON CHEMICAL INTERMEDIATES
(2021)
Article
Chemistry, Inorganic & Nuclear
Asanda C. Matsheku, Munaka C. Maumela, Banothile C. E. Makhubela
Summary: Researchers have designed new ligands for palladium-catalyzed carbon-carbon cross-coupling reactions, achieving good yields of reaction products. Moreover, remarkable activity of the catalysts under specific conditions has also been observed.
Article
Chemistry, Multidisciplinary
Hassan Keypour, Jamal Kouhdareh, Rahman Karimi-Nami, Idris Karakaya, Molood Abdollahi-Moghadam, Khadijeh Rabiei, Sedigheh Alavinia
Summary: This study presents the development and application of an environmentally compatible and recyclable heterogeneous catalyst for C-C coupling reactions. The catalyst demonstrated excellent catalytic performance with high yields of up to 98%. The synthetic method showed advantages such as simple set-up, improved yields, short reaction times, non-toxic solvents, catalyst durability, and high turnover frequency.
Article
Chemistry, Physical
Alexander F. Schmidt, Anna A. Kurokhtina, Elizaveta Larina, Elena V. Vidyaeva, Nadezhda A. Lagoda
Summary: The study reveals the independent selectivity in the Suzuki-Miyaura reaction, indicating the involvement of two distinct palladium species in the formation of biaryl compounds. This finding is consistent with the cooperative mechanism and challenges the traditional understanding of the reaction pathway.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Physical
A. A. Kurokhtina, E. Larina, E. V. Vidyaeva, N. A. Lagoda, A. F. Schmidt
Summary: The results of a kinetic study on the alkene activation step in the Mizoroki-Heck reaction indicate that alkenes participate in a fast step in the catalytic cycle, when reacting with unreactive aryl chlorides in a ligand-free palladium catalytic system.
KINETICS AND CATALYSIS
(2021)
Article
Chemistry, Applied
Nadezhda A. Lagoda, Elizaveta Larina, Elena V. Vidyaeva, Anna A. Kurokhtina, Alexander F. Schmidt
Summary: This study distinguishes between the homogeneous and heterogeneous catalytic mechanisms of Pd catalytic systems in the Suzuki-Miyaura reaction, providing convincing evidence for reactions proceeding simultaneously through both mechanisms. The use of ligand-free conditions suggests that the reaction proceeds in the solution phase through a homogeneous mechanism even when heterogeneous precursors are used, based on differential selectivity under competition conditions.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Physical
Elizaveta V. Larina, Anna A. Kurokhtina, Elena V. Vidyaeva, Nadezhda A. Lagoda, Alexander F. Schmidt
Summary: The study focused on the role of ionic Pd species in catalytic systems for cross-coupling reactions, specifically investigating the differential selectivity of the Mizoroki-Heck reaction with competition between aryl halides or alkenes. It was found that the additives of tertiary phosphine and halide salts significantly affect the catalytic activity of anionic Pd complexes, determining the regioselectivity of the reaction.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Physical
E. Larina, A. A. Kurokhtina, N. A. Lagoda, A. F. Schmidt
Summary: This paper presents the study results on changes in the composition of palladium complexes responsible for substrate activation in the Mizoroki-Heck reaction. The catalytic activity of palladium complexes was found to be influenced by the concentration ratio of a tertiary phosphine, alkali metal halide, and palladium catalyst precursor. Only phosphine-free palladium complexes containing halide anions in their coordination sphere played a decisive role in the formation of reaction products when threshold values of the concentration ratio between halide ions and the tertiary phosphine were achieved. The nature of the cation and anion of a halide salt added to the catalytic system was found to have a key effect on the differential selectivity of the formation of different products under noncompetitive conditions.
KINETICS AND CATALYSIS
(2022)
Article
Chemistry, Physical
Alexander F. Schmidt, Anna A. Kurokhtina, Elizaveta Larina, Elena V. Vidyaeva, Nadezhda A. Lagoda
MOLECULAR CATALYSIS
(2022)
Article
Physics, Atomic, Molecular & Chemical
A. F. Schmidt, A. A. Kurokhtina, E. Larina, N. A. Lagoda, T. A. Babenko
Summary: This paper presents the results of a kinetic study on the homogeneous and heterogeneous mechanisms of catalysis in the Suzuki-Miyaura reaction. The study explores the catalytic reaction of low-reactive substrates without the use of strong organic ligand additives. The results indicate the involvement of truly dissolved homogeneous forms of palladium in the solution.
RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY B
(2022)
Article
Chemistry, Physical
A. A. Kurokhtina, E. Larina, N. A. Lagoda, A. F. Schmidt
Summary: An operando kinetic study was conducted on the Mizoroki-Heck reaction with low-reactive aryl chlorides using the most practically attractive ligand-free catalytic systems. The results showed the decisive effect of catalyst transformations outside the catalytic cycle on the main catalytic reaction. The simulation results based on the hypothesis of cooperative catalysis qualitatively fit the experimental data, suggesting the importance of considering cooperative catalysis in the analysis of experimental results and the construction of reaction mechanisms.
KINETICS AND CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
N. A. Lagoda, A. A. Kurokhtina, E. Larina, E. V. Vidyaeva, A. F. Schmidt
Summary: The mechanism of the Suzuki-Miyaura reaction, traditionally believed to be linear, has been suggested to have a potential cooperative mechanism based on unconventional kinetic analysis, where the substrate and reagent are activated in two parallel catalytic cycles by different palladium intermediates to form the product. The low kinetic orders observed under ligand-free conditions also support the cooperative mechanism, indicating changes in the relative amount of catalyst in two parallel catalytic cycles and/or catalyst deactivation.
RUSSIAN CHEMICAL BULLETIN
(2021)
Article
Chemistry, Organic
N. A. Lagoda, E. V. Vidyaeva, E. Larina, A. A. Kurokhtina, A. F. Schmidt
Summary: This study describes a ligand-free catalytic system for cross-coupling reactions in the system of aryl halide, arylacetylene, and alkene.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
