Article
Multidisciplinary Sciences
Lara E. Zetzsche, Jessica A. Yazarians, Suman Chakrabarty, Meagan E. Hinze, Lauren A. M. Murray, April L. Lukowski, Leo A. Joyce, Alison R. H. Narayan
Summary: This study demonstrates the use of cytochrome P450 enzymes for biocatalytic cross-coupling reactions, enabling the formation of sterically hindered biaryl bonds through oxidative C-C bond formation. By engineering the substrate and atroposelectivity of the P450 enzyme, a highly efficient and selective process has been developed.
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
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)
Review
Chemistry, Multidisciplinary
Massimo C. D'Alterio, Eric Casals-Cruanas, Nikolaos V. Tzouras, Giovanni Talarico, Steven P. Nolan, Albert Poater
Summary: The story of C-C bond formation involves various reactions, with Suzuki-Miyaura reaction being one of the most outstanding ones. The focus is on the formation of catalytically active species, with preactivation potentially playing a role as the rate determining step in the overall reaction. Computational chemistry plays a key role in identifying the rate determining step and achieving milder conditions in experimental settings through predictive catalysis.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Sheng-Qi Qiu, Yu Chen, Xiang-Jun Peng, Shi-Jiang He, Jun Kee Cheng, Yong-Bin Wang, Shao-Hua Xiang, Jun Song, Peiyuan Yu, Junmin Zhang, Bin Tan
Summary: In this study, we achieved the arene-alkene Suzuki-Miyaura coupling reaction between hindered aryl halides and vinyl boronates by designing appropriate ligands and reaction parameters. The axially chiral acyclic aryl-alkenes obtained exhibited remarkable efficiency, enantioselectivity, and E/Z selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Fatemeh Mohajer, Majid M. Heravi, Vahideh Zadsirjan, Nargess Poormohammad
Summary: The Sonogashira reaction is a key cross-coupling reaction in organic synthesis, forming a C-C bond between a vinyl or aryl halide and a terminal alkyne. While traditionally requiring copper and phosphines or amines as co-catalysts and bases, recent developments have enabled the reaction to proceed without these components. This advancement could promote the principles of green chemistry and enhance the economic feasibility of the reaction.
Article
Chemistry, Physical
Talat Baran, Sema Akay, Berkant Kayan
Summary: The study demonstrated the potential of using Pd NPs@VT/Fe3O4 derived from volcanic tuff as a heterogeneous catalyst for the efficient synthesis of biaryl compounds via Suzuki-Miyaura coupling reactions, with a high yield of 99%. Furthermore, the catalyst showed stable and efficient catalytic performance even after eight consecutive cycles, with a yield of up to 92%.
Article
Chemistry, Physical
Chung-Hao Yang, Yi-Hung Liu, Shie-Ming Peng, Shiuh-Tzung Liu
Summary: A hetero-binuclear complex Ir-Pd was obtained by the reaction between iridium complex and (CH3CN)PdCl2 via ortho-metallation. This complex showed excellent catalytic activity for Suzuki-Miyaura and Sonogashira cross coupling reactions under blue LED irradiation. The effects of photochemical conditions on these coupling reactions catalyzed by Ir-Pd were studied.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Physical
Antonio J. LaPorte, Yao Shi, Jason E. Hein, Martin D. Burke
Summary: Stereospecific Csp(3) Suzuki-Miyaura cross-coupling simplifies the synthesis of stereochemically complex small molecules, but current methods are not compatible with complex building blocks commonly found in natural products and other complex targets. This study presents a method for embedding the alpha-methyl-beta-hydroxyl motif within stereochemically defined secondary alkyl boronic ester building blocks, allowing for stereospecific cross-coupling. The use of beta-aryloxysilyl groups addresses the decrease in reactivity and side reactions associated with beta-oxygen-containing Csp(3) boronic esters. Mechanistic studies reveal the activation of a dihydroxysiloxaborolate as a transmetalation partner in a stereospecific process that retains configuration.
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
Taruna Singh, Sushil Kumar, Natesan Thirupathi, Pramod Kumar
Summary: The influence of substituents on the aryl rings of thiourea on the structure of resulting compounds was investigated through the reaction of Pd(OAc)2 with N,N'-di(4-tolyl)thiourea and N,N'-bis(2-anisyl)thiourea. Bis-chelated complexes [Pd{& kappa;2(N, S)-(C(NAr)(S)(ArNH)}2] [Ar = C6H4Me-4 (1), C6H4(OMe)-2 (2)] were obtained in yields of 78% and 86%, respectively, when Pd(OAc)2 reacted with two equivalents of N,N & PRIME;-di(4-tolyl) thiourea and N,N'-bis(2-anisyl)thiourea in toluene at 60 degrees C. The catalytic efficacy of complexes 1 and 2 towards Suzuki-Miyaura reactions was investigated, and both exhibited fair to excellent catalytic ability at very low catalyst loading, with complex 2 showing relatively higher activity compared to complex 1.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Review
Chemistry, Multidisciplinary
Shelesh Krishna Saraswat, Ramanjaneyulu Seemaladinne, Media Noori Abdullah, Halim Zaini, Nabeel Ahmad, Nafis Ahmad, Esmail Vessally
Summary: Aryl fluorosulfates are versatile building blocks in organic synthesis and have gained increasing attention in SuFEx click chemistry. They can be easily prepared from phenols using low-cost sulfuryl fluoride as a sulfonyl fluoride provider. They have been used as less toxic and more atom economical alternatives to triflates in numerous cross-coupling reactions. This review summarizes the recent advances and developments in utilizing aryl fluorosulfates as electrophilic partners in cross-coupling reactions.
Article
Chemistry, Organic
Giorgio Rizzo, Gianluigi Albano, Teresa Sibillano, Cinzia Giannini, Roberta Musio, Fiorenzo G. Omenetto, Gianluca M. Farinola
Summary: This paper reports the application of a silk fibroin-supported Palladium catalyst (Pd/SF) in Suzuki-Miyaura and Ullmann coupling reactions of aryl chlorides. The existence of catalytic pockets where monoatomic palladium species can form stable complexes with SF is hypothesized and supported by experimental analysis. The size of the catalytic pocket of Pd/SF is estimated to be approximately 15 angstroms using computational modeling.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Chau Ming So, On Ying Yuen, Shan Shan Ng, Zicong Chen
Summary: This study presents a general chemoselective Suzuki-Miyaura coupling using a Pd/L33 catalyst, showing efficient coupling of polyhalogenated aryl triflates by controlling reactivity order and key factors, achieving high yields and chemoselectivity with low Pd catalyst loading.
Article
Chemistry, Organic
Jacob R. Ludwig, Eric M. Simmons, Steven R. Wisniewski, Paul J. Chirik
Summary: A cobalt-catalyzed method for the C(sp(2))-C(sp(3)) Suzuki-Miyaura cross coupling of aryl boronic esters and alkyl bromides was developed, with cobalt-ligand combinations being assessed through high-throughput experimentation. The use of cobalt(II) sources with trans-N,N'-dimethylcyclohexane-1,2-diamine (DMCyDA, L-1) resulted in optimal yield and selectivity. The transformation allowed for diverse steric and electronic properties on the aryl boronate nucleophile as well as various levels of branching and synthetically valuable functionality on the electrophile, with radical trap experiments supporting the formation of electrophile-derived radicals during catalysis.
Review
Chemistry, Multidisciplinary
Yuzhou Wu, Fedor Jelezko, Martin B. Plenio, Tanja Weil
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Roman Vasiuta, Herbert Plenio
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Multidisciplinary
Oliver Halter, Roman Vasiuta, Israel Fernandez, Herbert Plenio
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Multidisciplinary
Oliver Halter, Israel Fernandez, Herbert Plenio
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Multidisciplinary
Roman Savka, Marvin Bergmann, Yuki Kanai, Sabine Foro, Herbert Plenio
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Inorganic & Nuclear
Marvin Bergmann, Roman Savka, Sabine Foro, Herbert Plenio
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Roman Vasiuta, Alexander Stockert, Herbert Plenio
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Inorganic & Nuclear
Marvin Bergmann, Herbert Plenio
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2018)
Article
Chemistry, Inorganic & Nuclear
Oliver Halter, Herbert Plenio
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2018)
Article
Chemistry, Applied
Maximillian Heidrich, Marvin Bergmann, Dorian Mueller-Borges, Herbert Plenio
ADVANCED SYNTHESIS & CATALYSIS
(2018)
Article
Chemistry, Inorganic & Nuclear
Yuki Kanai, Sabine Foro, Herbert Plenio
Article
Chemistry, Physical
Natalie Peschek, Klaus-Juergen Wannowius, Herbert Plenio
Article
Physics, Atomic, Molecular & Chemical
Sara Hadjiali, Roman Savka, Markus Plaumann, Ute Bommerich, Sarah Bothe, Torsten Gutmann, Tomasz Ratajczyk, Johannes Bernarding, Hans-Heinrich Limbach, Herbert Plenio, Gerd Buntkowsky
APPLIED MAGNETIC RESONANCE
(2019)
Article
Chemistry, Multidisciplinary
O. Halter, H. Plenio
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Marvin Bergmann, Meike Egert, Herbert Plenio
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
