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.
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, Organic
Hideaki Kurabayashi, Tsunehisa Hirashita, Shuki Araki
Summary: Compound 1, a mesoionic compound, serves as a superior solvent for the Mizoroki-Heck reaction, yielding high product yield without the need for ligands. Various Heck-type coupling reactions were successfully performed in mesoionic liquid 1, and the catalysts could be reused multiple times with the addition of a phosphine ligand.
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, 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)
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
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
Xiaopeng Peng, Yang Yang, Bingling Luo, Shijun Wen, Peng Huang
Summary: A diverse set of fluorenes can be conveniently constructed starting from cyclic diaryliodoniums and terminal alkenes through Pd-catalyzed reactions. These reactions involve a conventional Mizoroki-Heck reaction and a reductive Heck reaction, with a general scope of alkenes leading to the synthesis of 29 fluorenes, expanding the structural diversity of fluorenes.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Alexey S. Kashin, Darya O. Prima, Daria M. Arkhipova, Valentine P. Ananikov
Summary: Using SEM and TEM techniques, the transformations of palladium-containing species in imidazolium ionic liquids are studied, revealing the correlation between the reactivity of aryl halides and the microdomain structure. It is found that the formation of a stable nanosized palladium phase is detected under the action of aryl halides capable of forming microcompartments. This work highlights the importance of considering both molecular and microscale properties in catalytic transformations.
Article
Chemistry, Multidisciplinary
Majid Mohammadnia, Nazanin Poormirzaei
Summary: A new magnetic nanocatalyst, Pd supported on 5-carboxyoxindole functionalized cell@Fe3O4 nanoparticles, was synthesized and successfully employed for the Heck-type arylation of different substituted maleimides. This green catalyst can be easily recovered and reused multiple times without significant loss of activity, providing a clean and efficient synthetic procedure.
NANOSCALE ADVANCES
(2021)
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, Multidisciplinary
Qi Meng, Huimin Zhang, Haiqun Chen, Qiaoqiao Teng
Summary: A polystyrene-supported palladium complex was prepared and showed significantly improved catalytic activity in Mizoroki-Heck reactions. The material functioned as a pre-catalyst, with soluble Pd(0) species generated under catalytic conditions as the actual catalyst, allowing for catalytic recycling.
Article
Chemistry, Multidisciplinary
Ksenia S. Egorova, Alexey S. Galushko, Lilya U. Dzhemileva, Vladimir A. Dyakonov, Valentine P. Ananikov
Summary: This work introduces a powerful approach for fast assessment of the potential biological impact of chemical processes on living organisms, utilizing bio-Profiles based on cytotoxicity data and bio-Factors for chemical reactions. Bio-Profiles visually determine substances' contributions to overall cytotoxicity, while bio-Factors indicate quantitative change in cytotoxicity during a process.
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, Organic
Swantje Lerch, Stefan Fritsch, Thomas Strassner
Summary: This study reports the use of TAAILs as solvents in the Mizoroki-Heck reaction. By optimizing the reaction conditions, efficient synthesis of (E)-stilbene derivatives with high yields was achieved. The catalytic system using TAAILs showed higher yields compared to other commercially available ionic liquids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)