Article
Chemistry, Inorganic & Nuclear
Mohammad Gholinejad, Hamid Esmailoghli, Faezeh Khosravi, Jose M. Sansano
Summary: A palladium catalyst supported onto an ionic liquid-modified carbon nanotube was prepared and studied for its application in copper-free Sonogashira-Hagihara coupling reactions. The heterogeneous catalyst was successfully recycled for 5 consecutive identical reactions while maintaining its efficiency.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Xiao-Qing Han, Lei Wang, Ping Yang, Jing-Yuan Liu, Wei-Yan Xu, Chao Zheng, Ren-Xiao Liang, Shu-Li You, Junliang Zhang, Yi-Xia Jia
Summary: A palladium-catalyzed intramolecular enantioselective Mizoroki-Heck reaction of naphthalenes has been developed, leading to the formation of a series of unique heterocyclic compounds with enantiomeric excess values retained. The reaction relies on the use of a chiral sulfonamide phosphine ligand to inhibit competitive and undesired reactions.
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
Chiara Palladino, Tommaso Fantoni, Lucia Ferrazzano, Beatrice Muzzi, Antonio Ricci, Alessandra Tolomelli, Walter Cabri
Summary: The copper-free Heck-Cassar-Sonogashira (HCS) reaction is a powerful method for C-C bond formation in organic synthesis and has several industrial applications. This study investigated the mechanism of the copper-free HCS reaction by conducting stoichiometric and catalytic reactions and analyzing the role of the base. The results showed that the base can accelerate the reduction of the precatalyst and decrease the energy barrier for the alkyne carbopalladation step.
Article
Chemistry, Organic
Mei-Ling Wang, Hui Xu, Han-Yuan Li, Biao Ma, Zhen-Yu Wang, Xing Wang, Hui-Xiong Dai
Summary: The Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is achieved via palladium-catalyzed ligand-promoted C-C bond cleavage, providing good to excellent yields of the alkene product. Further applications in the late-stage olefination of drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By using ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved through sequential ortho-C-H alkylation/ipso-Heck olefination.
Article
Chemistry, Multidisciplinary
Nina V. Kuchkina, Svetlana A. Sorokina, Alexey V. Bykov, Mikhail G. Sulman, Lyudmila M. Bronstein, Zinaida B. Shifrina
Summary: The use of PEGylated nanocomposite catalysts has successfully stabilized Pd2+ complexes and Pd nanoparticles, demonstrating excellent catalytic activity in copper-free Sonogashira and Heck cross-coupling reactions. The reactions exhibit high yields in green solvents with low palladium loading and allow for easy magnetic separation and reuse without significant decrease in catalytic activity.
Article
Chemistry, Organic
Fusheng Bie, Chengwei Liu, Michal Szostak, Xuejing Liu
Summary: A robust palladium-catalyzed decarbonylative alkynylation of aryl anhydrides is reported. The catalytic system of Pd(OAc)(2)/XantPhos and DMAP as a nucleophilic additive has been identified as effective promoters for decarbonylative Sonogashira alkynylation. The present process expands this reactivity to readily available aryl anhydrides as electrophilic reagents for decarbonylative alkynylation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Khadijeh Ghabdian, Alireza Motavalizadehkakhky, Rahele Zhiani, Majid M. Heravi, Ali Allahresani, Vahideh Zadsirjan
Summary: A Co(II) complex immobilized on a magnetic graphene oxide nanocomposite was synthesized and characterized by various techniques. The catalytic activity of this complex in Sonogashira cross-coupling reaction and Heck-Mizoroki coupling reaction was examined. The results showed that the complex exhibited high catalytic activity and could be easily recovered and reused.
JOURNAL OF CLUSTER SCIENCE
(2023)
Article
Chemistry, Physical
Zahid Nawaz, Nevin Gurbuz, Muhammad Naveed Zafar, Namik Ozdemir, Uzma Habib, Kalsoom Jan, Ismail Ozdemir
Summary: The research aims to synthesize homogeneous catalysts by starting from novel precursors to form N-heterocyclic carbene (NHC) ligands, and subsequently synthesizing Pd(NHC)-PEPPSI type complexes. The structure of all synthesized ligands and complexes was confirmed using various spectroscopic techniques, with some compounds confirmed by X-ray. These complexes were found to be significantly active as catalysts in the C-C cross-coupling reaction.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Polymer Science
Noriyuki Suzuki, Shun Koyama, Rina Koike, Nozomu Ebara, Rikito Arai, Yuko Takeoka, Masahiro Rikukawa, Fu-Yu Tsai
Summary: Thermoresponsive diblock copolymers were successfully synthesized and utilized in palladium-catalyzed coupling reactions in water. The study demonstrated higher efficiency in extraction for PDEAAm copolymers compared to PNIPAAm copolymers. Furthermore, aggregative precipitation of products in Sonogashira coupling reactions was observed, and washing the precipitate with water resulted in high purity products with good yields.
Article
Chemistry, Multidisciplinary
Chiara Palladino, Tommaso Fantoni, Lucia Ferrazzano, Alessandra Tolomelli, Walter Cabri
Summary: This study described the development of sustainable and efficient aryl halides with copper-free Heck-Cassar-Sonogashira (HCS) and Suzuki-Miyaura (SM) cross-coupling reactions. The use of N-hydroxyethylpyrrolidone (HEP)/water as solvents and sodium 2'-dicyclohexylphosphino-2,6-dimethoxy-1,1'-biphenyl-3-sulfonate (sSPhos) as a ligand produced the target products with high turnover number (TON), high reaction mass efficiency (RME), and low process mass intensity (PMI). The optimal conditions for HCS and SM coupling reactions were determined, and the achieved PMI and RME were among the best in the field, simplifying purification processes crucial for industrial applications.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(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
Chemistry, Applied
Si-Yu Tsai, Yu-Wen Huang, Chih-Ming Chou
Summary: A carboxylate-directed palladium-catalyzed Mizoroki-Heck alkenylation reaction of gamma,delta-unsaturated carboxylic acids with alkenyl bromides was reported. The carboxylate group effectively chelates to a Pd center, enabling the formation of conjugated 1,3-dienes with high stereoselectivity in the distal alkenylation of electronically unbiased internal alkenes. Additionally, the conjugated 1,3-diene products can be used for various synthetic applications.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Mujeeb Khan, Muhammad Ashraf, Mohammed Rafi Shaik, Syed Farooq Adil, Mohammad Shahidul Islam, Mufsir Kuniyil, Merajuddin Khan, Mohammad Rafe Hatshan, Riyadh H. Alshammari, Mohammed Rafiq H. Siddiqui, Muhammad Nawaz Tahir
Summary: In this study, a highly reduced graphene oxide-immobilized nanoparticle catalyst is used to catalyze Mizoroki-Heck cross-coupling reactions in water. The smart functionalization of the catalyst enhances dispersibility and stability, leading to higher conversion rates.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Physical
Carson Wiethan, Ingredy B. Braga, Vitor H. Menezes da Silva, Joao M. Batista Jr, Carlos Roque D. Correia
Summary: The enantioselective synthesis of isoindolones via Heck-Mizoroki reactions of endocyclic enamides using a palladium-bis(oxazoline) catalyst system is described. N,N-ligands prove to be an effective and low-cost alternative to phosphine-based chiral ligand counterparts. The intramolecular Heck reaction enables the construction of tricyclic isoindolones containing chiral centers in high yields and enantiomeric ratios.
Article
Chemistry, Applied
Mohammad Gholinejad, Mahmoud Afrasi, Carmen Najera
APPLIED ORGANOMETALLIC CHEMISTRY
(2019)
Review
Chemistry, Physical
Mohammad Gholinejad, Zhwan Naghshbandi, Carmen Najera
Article
Chemistry, Multidisciplinary
Mohammad Gholinejad, Zahra Rasouli, Carmen Najera, Jose M. Sansano
Article
Chemistry, Multidisciplinary
Abdollah Neshat, Mahmoud Afrasi, Shirin Gilanchi, Mohammad Gholinejad
Article
Chemistry, Applied
Mohammad Gholinejad, Zhwan Naghshbandi, Jose M. Sansano
APPLIED ORGANOMETALLIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Manel Chehrouri, Adil A. Othman, Cristina Moreno-Cabrerizo, Mohammad Gholinejad, Jose M. Sansano
MONATSHEFTE FUR CHEMIE
(2020)
Article
Chemistry, Multidisciplinary
Mohammad Gholinejad, Hamid Esmailoghli, Jose M. Sansano
CANADIAN JOURNAL OF CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Mohammad Gholinejad, Mohammad Shojafar, Jose M. Sansano
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Applied
Abdollah Neshat, Mohammad Gholinejad, Mahmoud Afrasi, Piero Mastrorilli, Stefano Todisco, Shirin Gilanchi, Farzane Osanlou
Summary: The product obtained by the reaction of deprotonation of 2-mercaptobenzothiazole or methimazole with copper iodide in the presence of tertiary phosphines showed high catalytic activity in coupling reactions. The investigation into the nature of active species emphasized the crucial role of organosulfur and organophosphorus compounds. The coupling reactions were successfully carried out at low catalyst loadings in water/THF with relatively short reaction times.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Mehdi Rezapour, Mohammad Abbasi, Mohammad Gholinejad
Summary: Type II photoelimination reactions are crucial in biological systems, and nitro substituents have unusual effects in aryl ketones. The low quantum yield for the formation of nitro substituent may be due to rapid deactivation of the carbonyl localized state. Research on these reactions is important in understanding their mechanisms and effects.
PHOTOCHEMISTRY AND PHOTOBIOLOGY
(2021)
Article
Chemistry, Physical
Abdollah Neshat, Mohammad Gholinejad, Hafize Ozcan, Faezeh Khosravi, Ali Mousavizadeh Mobarakeh, Omer Zaim
Summary: Synthesis and characterization of novel Schiff bases as bidentate ligands for stabilizing palladium ions in Suzuki cross-coupling reactions; investigation of catalytic activity and reaction scope with different aryl halides and boronic acids, showing promising results for specific palladium complexes.
MOLECULAR CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Ali Reza Amani-Ghadim, Abdolreza Tarighati Sareshkeh, Narges Nozad Ashan, Homa Mohseni-Zonouz, Seyed Masoud Seyed Ahmadian, Mir Saeed Seyed Dorraji, Mohammad Gholinejad, Farzaneh Bayat
Summary: A carbon-doped g-C3N4 (CGNS) nanocomposite with Ag2O and alpha-Fe2O3 was synthesized to enhance the photocatalytic activity for Acid Red 14 (AR14) degradation. The nanocomposite showed improved performance in the visible-light absorption range and effectively suppressed charge carrier recombination, leading to stable photocatalytic efficiency. Studies on scavengers revealed the influential role of superoxide anion radicals in AR14 degradation compared to hydroxyl radicals and holes, indicating the potential for practical applications.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Arezoo Mehdikhani, Mohammad Gholinejad, Abbasali Zamani, Jose M. Sansano
Summary: The study assessed the potential of imidazole modified clinochlore as a new adsorbent for removing Ibuprofen from polluted water. Characterization studies confirmed the convenience of Im@clin for adsorption, and the adsorption capacity was evaluated under different conditions. The thermodynamic parameters showed that the process of IBP adsorption by Im@clin is endothermic, spontaneous, and entropy derived.
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Mohsen Akbarian, Mohammad Gholinejad, Soliman Mohammadi-Samani, Fatemeh Farjadian
Summary: Mesoporous silica nanoparticles were synthesized and used as a fluorescence-based delivery system for the anticancer drug doxorubicin. The nanoparticles showed no cytotoxicity alone, but exhibited significant drug release and cytotoxicity against breast cancer cells when loaded with doxorubicin. The safety and biocompatibility of the particles were confirmed, making them suitable for therapeutic and imaging applications.
MICROPOROUS AND MESOPOROUS MATERIALS
(2022)
Review
Chemistry, Physical
Mohammad Gholinejad, Faezeh Khosravi, Mahmoud Afrasi, Jose M. Sansano, Carmen Najera
Summary: This review discusses the preparation and synthetic applications of bimetallic PdCu nanoparticles, highlighting their superior catalytic activity and selectivity compared to monometallic counterparts. Various preparation methods and support materials allow these nanomaterials to successfully perform a wide range of synthetic reactions and catalytic processes.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)