Article
Chemistry, Organic
Liang-Liang Yang, Jin Cao, Tian-Yuan Zhao, Shou-Fei Zhu, Qi-Lin Zhou
Summary: The highly enantioselective Si-H bond insertion reaction of alpha-aryldiazoacetates catalyzed by chiral spiro dirhodium tetraphosphate was successfully developed, leading to the preparation of various chiral alpha-silyl esters with high yield and excellent enantioselectivity. Even challenging substrates for other chiral dirhodium catalysts showed good results in this reaction, making it one of the few successful applications of chiral dirhodium phosphates in asymmetric catalysis.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Bin Lu, Xinyi Liang, Jinyu Zhang, Zijian Wang, Qian Peng, Xiaoming Wang
Summary: This study reports a three-component reaction enabled by dirhodium(II)/Xantphos catalysis to efficiently synthesize diverse alpha-quaternary alpha-amino acid derivatives. Mechanistic studies indicate that the transformation is achieved through a relay dirhodium(II)-catalyzed carbene insertion and allylic alkylation process.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Wen-Kui Yuan, Bing-Feng Shi
Summary: An unprecedented enantioselective synthesis of spiro-gamma-lactams was achieved using a simple Co-II/chiral spiro phosphoric acid binary system, resulting in high levels of enantioselectivity. Additionally, a concise synthesis of an aldose reductase inhibitor was successfully carried out under this system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Applied
Yuxue Cao, Guodu Liu
Summary: Chiral phosphoric acid has been a crucial catalyst in chemical synthesis for over five decades. However, a revolutionary approach using photocatalytic excitation of molecules to generate free radicals has emerged in recent years, surpassing the limitations of traditional organic synthesis methods. A significant area of research focuses on chiral phosphoric acid synergistic photocatalysis for enantioselective chemical synthesis, utilizing a bifunctional hydrogen-bonding catalyst.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Biochemistry & Molecular Biology
Xu Li, Ting Fan, Qingji Wang, Tongfei Shi
Summary: A density functional theory study was conducted to investigate the mechanism of asymmetric transfer hydrogenation (ATH) of imines catalyzed by an indium metal-organic framework (In-MOF). The study revealed that the imine and reducing agent are simultaneously adsorbed on the chiral phosphoric acid, leading to a proton transfer reaction. The study also found that the substituent groups on the imine and the polarity of the solvent significantly affect the reaction activity and enantioselectivity.
Article
Chemistry, Applied
Yasuaki Fukazawa, Vladimir Yu. Vaganov, Julia V. Burykina, Artem N. Fakhrutdinov, Ruslan I. Safiullin, Felix Plasser, Aleksandr E. Rubtsov, Valentine P. Ananikov, Andrei V. Malkov
Summary: The mechanism of metal-catalyzed asymmetric alkylation of indoles remains uncertain. In this study, the authors investigate the mechanism from both molecular and nano-level perspectives, revealing the role of water and catalyst precursor on reaction selectivity and performance.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Zhi-Han Chen, Tian-Zhen Li, Ning-Yi Wang, Xiao-Fang Ma, Shao-Fei Ni, Yu-Chen Zhang, Feng Shi
Summary: This study introduces a novel strategy for the enantioselective synthesis of axially chiral N,N'-bisindoles using chiral phosphoric acid-catalyzed formal cycloadditions. The synthesized compounds showed excellent yields and enantioselectivities, and exhibited cytotoxicity towards cancer cells. Moreover, they were also transformed into axially chiral phosphine ligands with high catalytic activity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Bing-Chao Da, Shao-Hua Xiang, Shaoyu Li, Bin Tan
Summary: The well-defined conformational properties of axially chiral compounds have brought extraordinary values to various bioactive molecules, advanced materials, organocatalysts, and chiral ligands in asymmetric transformations. Chiral phosphoric acids have shown high relevance in atroposelective synthesis and have been widely used in asymmetric Bronsted acid catalysis. The research interest in reaction chemistry of atropisomers has led to the development of efficient approaches for the preparation of key axially chiral structures.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Thiago A. Grigolo, Joel M. Smith
Summary: A practical protocol for the first regiodivergent asymmetric addition of aryl and alkenyl organometallic reagents to substituted N-alkyl pyridinium heterocycles is described. The couplings proceed with high regiochemical and stereochemical selectivities, and provide access to chiral 1,2,3- and 1,3,4-trisubstituted dihydropyridine products, controlled by judicious choice of nitrogen activating agent. To this end, a correlation was found between the parameterized size of the activating group and the C2/C4 regioselectivity in the couplings. The utility of the described chemistry was demonstrated in two concise asymmetric syntheses of (+)-N-methylaspidospermidine and (-)-paroxetine.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Ke-Wei Chen, Zhi-Han Chen, Shuang Yang, Shu-Fang Wu, Yu-Chen Zhang, Feng Shi
Summary: A new strategy has been developed for the highly atroposelective synthesis of N-N axially chiral indole scaffolds and bispyrroles, which can be used as chiral organocatalysts and exhibit potent anticancer activity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Robert J. Mayer, Harpreet Kaur, Sophia A. Rauscher, Joseph Moran
Summary: Metal ions can catalyze transamination under biologically relevant conditions, with Cu2+, Ni2+, Co2+, and V5+ identified as the most active. These ions primarily accelerate the reaction by stabilizing key imine intermediates or increasing the acidity of the bound imine. Direct metal ion-catalyzed amino group transfer is highly favored even in the absence of cofactors or protein catalysts under biologically compatible reaction conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Caifang Han, Wei Meng, Xiangqing Feng, Haifeng Du
Summary: Asymmetric intramolecular hydroalkoxylation is an important method for accessing optically active cyclic ethers. The cyclization of 2-vinylbenzyl alcohols can be catalyzed by B(C6F5)3 with low catalyst loading, resulting in high yields. A novel chiral boro-phosphate was developed to achieve high enantioselective hydroalkoxylation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Xue-Song Gu, Ying Xiong, Fan Yang, Na Yu, Pu-Cha Yan, Jian-Hua Xie, Qi-Lin Zhou
Summary: An iridium-catalyzed asymmetric hydrogenation method involving dynamic kinetic resolution was successfully developed using chiral spiro PNN-ligands containing a C5-substituted chiral oxazoline unit. This protocol, combined with simple dehydration, provides a straightforward approach to prepare enantiomerically enriched 3-aryloxy tetrahydrofurans, which are prevalent structural motifs in many approved drugs and clinical candidates.
Article
Chemistry, Multidisciplinary
Linlong Dai, Yuheng Liu, Qing Xu, Meifang Wang, Qiaohong Zhu, Peiyuan Yu, Guofu Zhong, Xiaofei Zeng
Summary: This paper presents a dynamic kinetic resolution method for the synthesis of axially chiral diaryl ethers. By using a Bronsted acid catalyzed atroposelective transfer hydrogenation (ATH) reaction, the desired diaryl ethers could be obtained in moderate to good chemical yields (up to 79%) and high enantioselectivities (up to 95% ee) under standard reaction conditions. These structural motifs are interesting precursors for further transformations and may have potential applications in the synthesis of chiral ligands or catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jan Sietmann, Mike Ong, Christian Mueck-Lichtenfeld, Constantin G. Daniliuc, Johannes M. Wahl
Summary: Asymmetric access to gamma-lactams was achieved using (1S,2R)-1-amino-2-indanol for chiral induction, with downstream stereoinduction up to 88:12 dr. Mechanistic analysis revealed a Curtin-Hammett scenario, supported by spectroscopic, crystallographic, and computational studies. The method allows for the synthesis of optically pure gamma-lactams, including those with all-carbon quaternary stereocenters, and is exemplified by the formal synthesis of drug molecules baclofen, brivaracetam, and pregabalin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Energy & Fuels
Nasrin Siraj Lopa, Mohammad Karbalaei Akbari, Di Wu, Francis Verpoort, Serge Zhuiykov
Summary: Sub-10 nm 2D SnO2-ZnO heterostructures were constructed on Au-modified SiO2/Si wafers using atomic layer deposition (ALD) for high-performance electrochemical supercapacitors (ESCs). The heterostructure electrode exhibited pseudocapacitive-type Faradaic redox reactions with good reversibility. It achieved a high specific capacitance (Cs) of 538.90 F g-1 at a scan rate and current density of 10 mV s-1 and 8.0 A g-1, respectively. The high energy storage capacity and excellent electrochemical robustness of the 2D heterostructure electrode were attributed to the nanoscale thickness, improved infiltration and intercalation/deintercalation, and enhanced redox activity of the heterostructure.
Article
Energy & Fuels
Habib Ullah, Zakir Ullah, Zafar A. K. Khattak, Mohsin Ali Marwat, Baoyi Yu, Hyung Wook Kwon, Hyun You Kim, Francis Verpoort
Summary: Transforming atmospheric CO2 into industrially valuable cyclic carbonates is important for reducing CO2 concentration. Ruthenium catalysts with ONN pincer-type hydrazone ligands were synthesized and tested for CO2 valorization. These complexes showed improved catalytic performance, with a high turnover frequency of 833 h^-1 and >99% selectivity at atmospheric pressure without any cocatalyst.
Article
Energy & Fuels
Pongpon Teerachawanwong, Waralee Dilokekunakul, Poomiwat Phadungbut, Nikom Klomkliang, Somsak Supasitmongkol, Somboon Chaemchuen, Francis Verpoort
Summary: Metal-organic frameworks (MOFs) MIL-100 (Cr, Fe) synthesized by the hydrothermal method were subjected to heat treatment under an H(2 )flow, which enhanced crystallinity and exhibited superior CO2 adsorption capacity. The adsorption mechanism at a molecular level was examined using the grand canonical Monte Carlo method, and the heat contribution of each atom type was determined.
Article
Chemistry, Physical
Sadia Aroob, Sonia A. C. Carabineiro, Muhammad Babar Taj, Ismat Bibi, Ahmad Raheel, Tariq Javed, Rana Yahya, Walla Alelwani, Francis Verpoort, Khanita Kamwilaisak, Saleh Al-Farraj, Mika Sillanpaa
Summary: In this study, CuO nanoparticles were synthesized by a simple, one-pot mechanochemical approach using the leaf extract of Seriphidium oliverianum as a reducing and stabilizing agent. The CuO NPs showed high potential for degrading water-soluble industrial dyes, with degradation rates of 65.231% +/- 0.242 for methyl green (MG) and 65.078% +/- 0.392 for methyl orange (MO). This bio-mechanochemically synthesized CuO NPs are promising candidates for efficient dye removal from water.
Article
Chemistry, Physical
Noor Aljammal, Jeroen Lauwaert, Bert Biesemans, Francis Verpoort, Philippe M. Heynderickx, Joris W. Thybaut
Summary: Quantitative assessment of the potential benefits of microwave irradiation for fructose dehydration into 5-hydroxymethylfurfural (5-HMF) was conducted over a sulfonated metal-organic framework (MOF), MIL 101(Cr)-SO3H. The study investigated the effects of temperature, batch time, and catalyst-to-substrate ratio on the reaction. The results showed that microwave irradiation significantly enhanced the fructose conversion and yield of 5-HMF compared to conventional heating, with an eight-fold rate coefficient enhancement.
Article
Chemistry, Physical
Alireza Pourvahabi Anbari, Shima Rahmdel Delcheh, Philippe M. Heynderickx, Somboon Chaemcheun, Serge Zhuiykov, Francis Verpoort
Article
Chemistry, Multidisciplinary
Sheereen Afaq, Muhammad Usman Akram, Wasif Mahmood Ahmed Malik, Muhammad Ismail, Abdul Ghafoor, Muhammad Ibrahim, Mehr un Nisa, Muhammad Naeem Ashiq, Francis Verpoort, Adeel Hussain Chughtai
Summary: In this study, a novel acyl-amide-containing tetracarboxylate ligand was synthesized and used for the design of MOFs with guest accessible functional organic sites. The prepared MOF showed superior catalytic activity for Knoevenagel condensation and could be easily recovered and recycled.
Article
Nanoscience & Nanotechnology
Mohammad Karbalaei Akbari, Francis Verpoort, Jie Hu, Serge Zhuiykov
Summary: Acoustic-activated polarization at 2D domains provides supplementary mechanisms for adjusting orbitals at material heterointerfaces, activating various physicochemical applications. In this study, piezoelectric nanodomains were grown on the nonpolar 2D surface of liquid Ga-based nanoparticles, enabling highly efficient CO2 conversion. The controlled growth of selenium-rich piezoelectric nanodomains and the presence of carbon nanotube frameworks play important roles in enhancing the catalytic performance.
ACS APPLIED MATERIALS & INTERFACES
(2023)
Review
Chemistry, Applied
Farah Naz, Rahaman M. Abdur, Fatima Mumtaz, Mirella Elkadi, Francis Verpoort
Summary: This study reviews the application of heterogeneous catalysts in the ring-opening polymerization of cyclic esters, with a focus on metal-organic frameworks (MOFs) and supported catalysts. The importance of precise design and catalyst stability is emphasized in controlling polymerizations.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Zhan Chen, Jing Hang, Song Zhang, Ye Yuan, Francis Verpoort, Cheng Chen
Summary: This study designed and fabricated a series of Ru-containing heterogeneous catalysts, among which Ru-0.05@Co-NC exhibited the best catalytic performance, affording a variety of carboxylic acid products from aromatic or aliphatic alcohols in moderate to high yields. The catalyst showed excellent recyclability and could be conveniently and quickly recovered.
Article
Chemistry, Physical
Ipsita Nath, Jeet Chakraborty, Reinaud Lips, Sander Dekyvere, Jiang Min, Rajender S. Varma, Francis Verpoort
Summary: High-performing metal-free pH-universal HER catalysts are smarter options for producing carbon-free green fuels via water electrolysis. In this study, an indigo-based organic conjugated porous polymer with surface-decorated hydrogen bonding sites was developed, which exhibited promising electrochemical HER activity in acidic, alkaline, and neutral media. The material showed comparable performance to contemporary metal-free carbonaceous electrocatalysts and state-of-the-art metal-based catalytic systems, with an overpotential of only 28 mV at 10 mA cm(-2) current density under appropriate conditions.
JOURNAL OF MATERIALS CHEMISTRY A
(2023)
Article
Energy & Fuels
Somboon Chaemchuen, Xiaotong Hou, Zhonghan Cheng, Kui Zhou, Serge Zhuiykov, Francis Verpoort
Summary: A facile method of obtaining zinc anchored in a nitrogen-doped carbon matrix (Zn-NCx) from solid precursors via the solid-solid thermal (SST) route was developed. The synthesis of Zn-NCx was completed under single-step and solvent-free conditions. The zeolitic-imidazole framework (ZIF-8) was first fabricated and sacrificed during the SST process to obtain Zn-NCx.
Article
Green & Sustainable Science & Technology
Wei-Ting Chen, Justin Chun-Te Lin, Shih-Hsiung Chen, Francis Verpoort, Kun-Liang Hong, Rao Y. Surampalli, Chih-Ming Kao
Summary: This research developed an innovative electrolyzed catalytic system to produce nanobubble-infused catalytic water for remediating diesel oil-contaminated soils. The results demonstrated that this nanobubble-infused catalytic water could effectively remove pollutants while minimizing the risk of secondary pollution.
JOURNAL OF CLEANER PRODUCTION
(2023)
Article
Environmental Sciences
Wing-Sze Ho, Wei-Han Lin, Francis Verpoort, Kun-Liang Hong, Jiun-Hau Ou, Chih-Ming Kao
Summary: A novel electrolyzed catalytic system was developed to produce nanobubble-contained electrolyzed catalytic water for the remediation of petroleum-hydrocarbon-contaminated soils and groundwater. The system effectively removed petroleum hydrocarbons from soils and decreased their concentration in groundwater by generating high concentrations of nanobubbles and radicals.
JOURNAL OF ENVIRONMENTAL MANAGEMENT
(2023)
Article
Energy & Fuels
Somboon Chaemchuen, Zhonghan Cheng, Xiaotong Hou, Francis Verpoort, Jakkapan Kumsi, Nikom Klomkliang
Summary: This paper presents a synthesis method for bimetallic nickel/zinc embedded in N-doped carbon through solid-solid thermal method. The resulting material exhibits a robust carbon structure and shows efficient CO2 adsorption potential compared to commercial activated charcoal.