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, Multidisciplinary
Julius Hoepfner, Marius Brehm, Pavel A. Levkin
Summary: The rising costs of pharmaceutical research are currently limiting the productivity of drug discovery and development, but can potentially be reduced through miniaturization of compound synthesis and screening. In this study, the influential palladium-catalyzed Suzuki-Miyaura reaction is successfully implemented at the nanoliter scale on droplet microarrays for the synthesis of an 800-compound library of biphenyls. The synthesis of these compounds requires minimal reagents and solvent volume, and the obtained compounds can be purified and cleaved from excess reactants and catalyst. This novel approach expands the capabilities of droplet microarrays for miniaturized high-throughput chemical synthesis and opens up possibilities for future synthesis and screening of chemical compounds in a single platform.
Article
Chemistry, Applied
Kanticha Khomthawee, Nattaporn Nilada, Antika Homchuen, Pranorm Saejueng
Summary: The CS-EDTA-Pd catalyst was prepared by dissolving chitosan and EDTA in acetic acid, forming beads, adsorbing palladium(II), and reducing it to palladium(0) with ethanol reflux. The catalyst was characterized by various techniques. It was then tested in the Suzuki-Miyaura cross-coupling reaction and showed good catalytic activity. The catalyst is inexpensive, easy to prepare, and can be reused multiple times with only a slight loss in product yields.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Angus Olding, Curtis C. Ho, Allan J. Canty, Nigel T. Lucas, James Horne, Alex C. Bissember
Summary: This study reports the synthesis of a family of unprecedented arylpalladium(II) boronates that are kinetically stable at ambient temperature, and their chemical competence in a Suzuki-Miyaura reaction was demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(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)
Article
Polymer Science
Noelia Esteban, Miguel Claros, Cristina Alvarez, Angel E. Lozano, Camino Bartolome, Jesus M. Martinez-Ilarduya, Jesus A. Miguel
Summary: A new set of microporous organic polymers (POPs) with high microporosity and moderate thermal stability has been synthesized via Friedel-Crafts knitting. These polymers, containing diphosphine derivatives, act as efficient catalysts for Suzuki-Miyaura coupling reactions, exhibiting excellent recyclability.
Article
Chemistry, Multidisciplinary
Matteo Albino, Thomas J. Burden, Carmen C. Piras, Adrian C. Whitwood, Ian J. S. Fairlamb, David K. Smith
Summary: The increase in demand and low abundance of palladium pose a significant threat to its future availability, making research into sustainable palladium-based technologies crucial. This study reports the development of Pd scavenging hybrid gel beads composed of agarose and a low-molecular-weight gelator based on DBS-CONHNH2. These mechanically robust gel beads exhibit potential as practical catalysts for Suzuki-Miyaura cross-coupling reactions, demonstrating good reusability, green metrics, and improved reaction times compared to previous examples. The leaching of palladium is almost completely eliminated and a detailed investigation explains how the nanoparticles are formed in situ. These ligand-free gel beads can be considered as robust nonligated heterogeneous PdNP catalysts with potential for the development of easily used chemical reaction systems.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
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.
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, Multidisciplinary
Robin Schulte, Sandra Afflerbach, Thomas Paululat, Heiko Ihmels
Summary: Molecular solar thermal energy storage (MOST) systems using phenyl- and naphthyl-linked bis- and tris-norbornadienes show high energy densities and have potential for efficient solar energy conversion and storage. These substrates were synthesized using Suzuki-Miyaura coupling reactions and their absorption properties and characteristics for MOST applications were investigated. The norbornadiene derivatives showed absorption onsets at 386 nm and photoisomerization quantum yields of 56% per photoisomerization event. The resulting quadricyclane products have half-lifes up to 14 days and very high energy densities of up to 734 kJ/kg.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Yiyang Zhang, Hong Sun, Yonghuai Yang, Haofei Li, Yaocheng Shi, Lei Yu
Summary: The catalytic activities of palladium nanoparticles on a polyaniline support were improved by tungsten doping, resulting in a significantly increased catalyst turnover number (>10(4)) for the Suzuki-Miyaura coupling reaction. Characterization of the materials showed that tungsten doping improved the micro-morphology, leading to more efficient absorption of reactants. Additionally, tungsten facilitated stabilization of Pd(0) species and the transmetallation step, both crucial for the catalytic reaction. Therefore, Pd/W@PANI engineering material may serve as a highly efficient heterogeneous catalyst in the pharmaceutical industry.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Physical
Elvis N. Nishida, Elder C. Leopoldino, Laize Zaramello, Higor A. Centurion, Renato Goncalves, Ricardo F. Affeldt, Carlos E. M. Campos, Bruno S. Souza
Summary: A novel Pd(II)-polymeric pre-catalyst was successfully prepared and demonstrated good activity in the Suzuki-Miyaura coupling reaction. The catalyst showed recyclability and its performance was affected by the concentration of the cross-coupling partners. The presence of oxygen was found to be crucial in preventing the formation of inactive Pd(0) aggregates.
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, Inorganic & Nuclear
Ceren Akpunar, Namik Ozdemir, Mert Olgun Karatas, Bulent Alici, Ismail Ozdemir
Summary: In this study, we synthesized five new coumarin-functionalised PEPPSI type Pd-NHC complexes to examine their catalyst properties. The complexes showed slightly distorted square-planar geometry and exhibited catalytic activity in the Suzuki-Miyaura reaction of phenylboronic acid and aryl bromide derivatives.
INORGANIC CHEMISTRY COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Matthew J. Andrews, Sebastian Brunen, Ruaraidh D. McIntosh, Stephen M. Mansell
Summary: This paper describes the synthesis and catalytic testing of a palladium complex with a 5-membered chelating [N,O] ligand, derived from the condensation of 2,6-diisopropylphenyl aniline and maple lactone. The catalyst was active towards the Suzuki-Miyaura cross-coupling reaction, and its activity was optimised through the selection of base, solvent, catalytic loading and temperature. The catalyst exhibited good activity towards aryl bromides with electron-withdrawing groups, as well as a range of boronic acids and pinacol esters. It was also a capable catalyst for the cross-coupling of aryl chlorides and phenylboronic acid.
Article
Chemistry, Applied
Jeanne L. Bolliger, Miriam Oberholzer, Christian M. Frech
ADVANCED SYNTHESIS & CATALYSIS
(2011)
Article
Chemistry, Applied
Miriam Oberholzer, Roman Gerber, Christian M. Frech
ADVANCED SYNTHESIS & CATALYSIS
(2012)
Article
Chemistry, Multidisciplinary
Marco Fetz, Roman Gerber, Olivier Blacque, Christian M. Frech
CHEMISTRY-A EUROPEAN JOURNAL
(2011)
Article
Chemistry, Multidisciplinary
Roman Gerber, Christian M. Frech
CHEMISTRY-A EUROPEAN JOURNAL
(2011)
Article
Chemistry, Multidisciplinary
Roman Gerber, Christian M. Frech
CHEMISTRY-A EUROPEAN JOURNAL
(2012)
Article
Chemistry, Multidisciplinary
Roman Gerber, Miriam Oberholzer, Christian M. Frech
CHEMISTRY-A EUROPEAN JOURNAL
(2012)
Article
Chemistry, Multidisciplinary
Miriam Oberholzer, Christian M. Frech
Article
Multidisciplinary Sciences
Miriam Oberholzer, Christian M. Frech
JOVE-JOURNAL OF VISUALIZED EXPERIMENTS
(2014)
Correction
Chemistry, Inorganic & Nuclear
Roman Gerber, Olivier Blacque, Christian M. Frech
DALTON TRANSACTIONS
(2011)