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
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
Nastaran Bagherzadeh, Ali Reza Sardarian, Hassan Eslahi
Summary: The magnetic nanocatalyst Fe3O4@SiO2-Phen-Pd(0) with powerful phenanthroline ligand was characterized and found suitable for Suzuki-Miyaura type C-C couplings using arylboronic acid derivatives as precursors, resulting in impressive data.
MOLECULAR CATALYSIS
(2021)
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, Inorganic & Nuclear
Mitat Akkoc, Nesrin Bugday, Serdar Altin, Nadir Kiraz, Sedat Yasar, Ismail Ozdemir
Summary: A novel magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was successfully prepared and demonstrated excellent catalytic activity for Suzuki-Miyaura cross-coupling reactions. The catalyst showed high stability and could be easily recovered and reused multiple times without significant loss of catalytic activity.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
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, 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, Applied
Seyed Mohammad Hossein Shirazi, Javad Mokhtari, Zohreh Mirjafary
Summary: The study introduced a novel approach for the preparation of abiraterone drug using a new heterogeneous palladium catalyst Pd-NPs@Zn-MOF, synthesized by encapsulation in nanoporous metal-organic framework Zn-MOF under temperature control program. The Pd-NPs@Zn-MOF was characterized by various techniques, including TEM, XRD, BET, ICP-OES, and XPS.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Houda Maati, Othmane Amadine, Younes Essamlali, Boutaina Rezki, Ikram Ayouch, Hassan Mahi, Karima Abdelouahdi, Mohamed Zahouily
Summary: A palladium ceria-zirconia Pd0.05Ce0.5Zr0.475O2 catalytic based nanomaterial was synthesized and characterized. Compared to other materials, Pd0.05Ce0.5Zr0.475O2 exhibited the highest BET surface area and showed high catalytic activity and stability for aryl bromides without the use of any ligand.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Applied
Maryam Mohammadikish, Nazanin Mosleh
Summary: Utilizing sunlight as a driving force in chemical reactions is beneficial for sustainability. This study reports the synthesis of a graphitic-carbon nitride system modified with Pd nanoparticles, which exhibits prominent photocatalytic performance for Suzuki-Miyaura coupling reactions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Engineering, Chemical
Yifan Jiang, Bingqi Xie, Jisong Zhang
Summary: This study systematically investigated the application of a heterogeneous palladium catalyst based on activated carbons (AC) in the Suzuki-Miyaura reaction of aryl halides with phenylboronic acid. The variations of reaction processing were studied using batch and continuous-flow procedures. The heterogeneous catalysts exhibited excellent reactivity and recyclability in batch mode, but significant dehalogenation and Pd leaching were observed in continuous-flow mode, leading to a decline in reaction selectivity and durability of the catalysts. Additionally, the reactivity and durability of the heterogeneous Pd catalysts with thiol-and amino-modified AC supports differed in batch and continuous-flow mode due to the difference in interaction between Pd species and AC supports.
CHINESE JOURNAL OF CHEMICAL ENGINEERING
(2023)
Article
Chemistry, Applied
Liam Byrne, Christian Skold, Per-Ola Norrby, Rachel H. Munday, Andrew R. Turner, Peter D. Smith
Summary: The development of biaryl 2,5-diphenylphospholanes as a new class of C-2-symmetric, monodentate ligands for asymmetric Suzuki-Miyaura (ASM) reactions has led to the successful preparation of a range of atropisomeric biaryl and heterobiaryl products with good to excellent levels of enantioselectivity. DFT studies indicate that the formation of a constraining ligand pocket and coordination of one of the biaryl methoxy groups to the metal center in the optimized ligands are crucial for restricting conformational freedom in the bond-forming step.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemistry & Molecular Biology
Qian Xie, Jing Li, Xiaoming Wen, Yanxia Huang, Yunchi Hu, Qing Huang, Guohai Xu, Yongrong Xie, Zhonggao Zhou
Summary: In this study, four new metal complexes containing carbohydrate-substituent N-heterocyclic carbenes (Carb-NHCs) were synthesized and evaluated for their catalytic activities in the Suzuki-Miyaura reaction. It was found that complex 2d exhibited the highest catalytic activity and yielded the products with high yields.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Shiguang Pan, Cong Gao, Jiatong Gui, Beibei Hu, Lifeng Gai, Changsheng Qiao, Chengwei Liu
Summary: A hierarchical titanium dioxide microspheres-supported palladium catalyst (Pd/TiO2-350) was successfully prepared and characterized. The Pd immobilization on TiO2 was confirmed with a palladium loading of 0.1 mmol g(-1) by ICP-OES analysis. Pd/TiO2-350 efficiently catalyzed the Suzuki-Miyaura reaction and could be reused multiple times without significant loss of activity, with a decreased loading of palladium species to 0.001 mol% and high turnover number and turnover frequency of 99,000 and 0.57 s(-1), respectively.
ARABIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Physical
Alexander F. Schmidt, Anna A. Kurokhtina, Elizaveta Larina, Nadezhda A. Lagoda
Summary: Despite extensive studies on the reaction of Pd intermediates in the Suzuki-Miyaura reaction (SMR), direct evidence supporting the widely accepted assumptions regarding the activity of Pd hydroxo complexes is lacking. This study presents results on the reactivity of Pd-OH and/or Pd-OR-containing complexes in the transmetalation step under ligand-free turnover conditions. The catalytic involvement of specific Pd species was determined under real catalytic conditions by measuring the selectivity of competing reactions.
MOLECULAR CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Da-Liang Zhu, Shan Jiang, David James Young, Qi Wu, Hai-Yan Li, Hong-Xi Li
Summary: In this study, a catalyst-free visible-light-driven C(sp(2))-H arylation of unprotected phenols with arylbromides was developed to obtain 2-arylated phenols. This reaction occurs through the excitation of an electron donor-acceptor complex between a phenolate and an arylbromide, electron transfer, and debrominative C(sp(2))-C(sp(2)) coupling.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Shan Jiang, Zi-Tong Zhang, David James Young, Lu-Lu Chai, Qi Wu, Hong-Xi Li
Summary: A photoinduced nickel-catalyzed cross-coupling reaction of arylsulfinates with (hetero)aryl halides has been achieved using visible light. The reaction showed a broad substrate scope and good functional group tolerance, providing diarylsulfones in moderate to excellent yields. The mechanism involves oxidative addition, single-electron oxidation, reductive elimination, and electron transfer.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Lu-Lu Chai, You-Hui Zhao, David James Young, Xinhua Lu, Hong-Xi Li
Summary: A photocatalytic system has been developed for the acceptorless dehydrogenation esterification of phenols and aromatic aldehydes, which shows great tolerance towards functional groups and high efficiency. It also exhibits high activity in the hydrogen-evolution cross coupling of aliphatic aldehydes and phenols.
Article
Chemistry, Multidisciplinary
Jixian Wang, Lei Li, Shan Jiang, David J. Young, Zhi-Gang Ren, Hong-Xi Li
Summary: This study presents a series of SH-group-functionalized covalent organic frameworks (COFs) as prospective photoactive materials for photocatalytic hydrogen evolution. The use of nickel thiolate as a cocatalyst significantly enhances the hydrogen evolution rate.
Article
Biochemistry & Molecular Biology
Wei Yang, Shengnan Hu, Yuwei Wang, Sisi Yan, Xiang-Qian Cao, Hong-Xi Li, David James Young, Zhi-Gang Ren
Summary: A new Ag/Cu bimetallic cluster exhibited strong phosphorescent emission at 644 nm and red-shifted emission at 678 nm upon removal of coordinated EtOH molecules. The structure and emission of the cluster were restored on exposure to EtOH vapor. The cluster also showed vapor-chromic phosphorescent response to common organic solvent vapors and a reusable PMMA film was developed as a visible sensor for MeCN.
Article
Chemistry, Medicinal
Mengyao Feng, Fuyuan Liu, Ningwen Yang, Jiayao Yu, Wei Yang, David James Young, Xiang-Qian Cao, Hong-Xi Li, Zhi-Gang Ren
Summary: A heterobimetallic coordination polymer [Au4(dppmt)4(AgCl)2]n (1) incorporating an in situ generated P-S ligand (dppmtH) was synthesized. The structure of 1 contains a one-dimensional helical Au-Au chain. Coordination polymer 1 exhibited a rapid, selective, reversible, and visible vapor chromic response on exposure to methanol (MeOH) vapor.
ACS MEDICINAL CHEMISTRY LETTERS
(2023)
Review
Chemistry, Organic
Da-Liang Zhu, Jie Li, David James Young, Yanqing Wang, Hong-Xi Li
Summary: Organic transformations using carbonyl-photoredox/metal dual catalysis have gained significant attention lately. Carbonyl photosensitizers, which are abundant and inexpensive, act as effective agents for single electron, energy, or hydrogen atom transfer to induce metal-catalyzed cross-coupling and dicarbofunctionalization of olefins. This review summarizes literature reports on metal-catalyzed photocatalytic coupling reactions from 2020 to mid-2023, focusing on C-C and C-heteroatom bond forming reactions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Jia-Jun Yan, Yu Wu, Weijia Zhai, Ningwen Yang, Hong-Xi Li, Wei Yang, Chengrong Lu, David James Young, Zhi-Gang Ren
Summary: The reaction of CF3COOAg, 3-bdppmapy and HTZ in CH2Cl2/MeOH resulted in a dinuclear Ag/P/S complex [Ag-2(TZ)(2)(3-bdppmapy)(2)]& BULL;xSol (1 & BULL;xSol). Crystals of 1 & BULL;xSol converted to 1 & BULL;2MeOH in air at room temperature and further to 1 under vacuum upon heating. The solid-state, room-temperature photoluminescent emission of 1 & BULL;xSol (510 nm) shifted to 494 nm (1 & BULL;2MeOH) and 486 nm (1).
Article
Chemistry, Organic
Da-Liang Zhu, Jie Li, David James Young, Yanqing Wang, Hong-Xi Li
Summary: This paper presents a mild strategy for aminating aryl halides with anilines using dual photoredox and nickel catalysis. Thioxanthen-9-one, an inexpensive and readily available compound, greatly enhanced this cross-coupling reaction, yielding a diverse range of diarylamines in good yields (41-93%) at room temperature. The reaction could be performed under compact fluorescent lamp light or sunlight and was tolerant of various functional groups. It was successfully applied to the synthesis of natural products and drug molecules, even at a gram-scale. The mechanism involves several steps including oxidative addition, transmetalation, energy transfer, and reductive elimination.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Shengnan Hu, Sisi Yan, Yuanyuan Hu, David James Young, Hong-Xi Li, Chengrong Lu, Jing-Hui He, Zhi-Gang Ren
Summary: Reliable and sensitive detection of sub-ppm level, ultra-low humidity is critical for a number of important technologies. We report a heteronuclear Au2Cu2 cluster complex that can undergo reversible transformations and has photoluminescent properties in different environments. The crystals of the complex can detect ultralow humidity of 0.21 ppm (w/w).
INORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
You-Hui Zhao, Hai-Yan Li, David James Young, Xiangqian Cao, Da-Liang Zhu, Zhi-Gang Ren, Hong-Xi Li
Summary: Earth-abundant copper(I) coordination complexes have been developed as visible-light photocatalysts for the intermolecular atom-transfer radical addition reactions. Four heteroleptic bis-chelate Cu(I) complexes were synthesized and showed broad absorption in the visible spectrum. These complexes facilitated efficient reactions with CBr4, CCl3Br, and CHI3, yielding high product yields up to 91%. The substitution on the phpz ligand had a significant impact on the absorption, emission, redox potential, and photocatalytic activity.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Mengyao Feng, Fuyuan Liu, Ningwen Yang, Jiayao Yu, Wei Yang, David James Young, Xiang-Qian Cao, Hong -Xi Li, Zhi-Gang Ren
Summary: A heterobimetallic coordination polymer [Au-4(dppmt)(4)(AgCl)2(]) n (1) with an in situ generated P-S ligand (dppmtH) was synthesized. The structure of 1 contains a helical Au-Au chain connected by [Au(2()dppmt)(2)] dimers. Upon excitation at 343 nm, 1 exhibited cyan phosphorescent emission at QY = 22.3% and t = 0.78 μs. Coordination polymer 1 exhibited a rapid, selective, reversible, and visible vaporchromic response on exposure to methanol vapor, with its emission shifting to a more intense green at QY = 46.8% and t = 1.24 μs.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Qi Wu, You-Hui Zhao, Chai Lu-Lu, Hai-Yan Li, Hong-Xi Li
Summary: The activation of stronger C(non-acyl)-S bond of thioesters for metal- and photoredox catalyst-free visible-light-mediated pyridylthioesterification of styrenes has been reported, showing excellent chemo- and regio-selectivity. This protocol is atom-economical, tolerant to various functional groups, and can be used for gram-scale reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Shan Jiang, Zi-Tong Zhang, David James Young, Lu-Lu Chai, Qi Wu, Hong-Xi Li
Summary: In this study, a photoinduced nickel-catalyzed cross-coupling reaction was achieved with moderate to excellent yields of arylsulfinates and (hetero)aryl halides. The reaction demonstrated a broad substrate scope and good functional group tolerance, leading to the formation of diarylsulfones. The mechanism involved several steps, including oxidative addition, oxidation, reductive elimination, and release of the product. The photoredox and nickel catalytic cycles interacted through electron transfer.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Inorganic & Nuclear
Yanhui Tao, Yuwei Wang, Shengnan Hu, David James Young, Chengrong Lu, Hong-Xi Li, Zhi-Gang Ren
Summary: The trinuclear complex [Au2Ag(dppmaphen)(2)(CN)(2)]PF6 emits light when exposed to low molecular weight alcohols, likely due to interactions between the analyte and the -PPh2 group. The photoluminescence can be quenched by removing or replacing the analyte, leading to a visible, rapid, and recyclable on/off switching effect.
DALTON TRANSACTIONS
(2021)
