Article
Chemistry, Multidisciplinary
Changli He, Xiaoxue Tang, Xin He, Yuqiao Zhou, Xiaohua Liu, Xiaoming Feng
Summary: Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles to beta-nitroenones or beta-nitroacrylates was achieved with chiral scandium catalysts. Functionalized 3,3-disubstituted oxindoles, including terminal and internal vinyl groups, were constructed in excellent yields and ee values.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Applied
Brigita Mudrakova, Peter Kisszekelyi, Denisa Vargova, Dorota Zakiewicz, Radovan Sebesta
Summary: This paper presents a highly enantio- and diastereoselective tandem transformation method, using Cu-catalyzed conjugate addition of Grignard reagents to heterocyclic Michael acceptors, followed by one-pot trapping of in situ formed enolates with stabilized carbocations or their equivalents. This method allows the installation of structurally attractive substituents on heterocyclic compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Jessica Wahlers, Michael Maloney, Farbod Salahi, Anthony R. Rosales, Paul Helquist, Per-Ola Norrby, Olaf Wiest
Summary: This study developed and applied a TSFF method to predict the stereoselectivity of aryl boronic acids conjugate addition to enones, achieving good results through automated screening and validation. Detailed error analysis and identification of structural origins for outliers were conducted. The results showed that the majority of virtual screening outcomes were in line with expectations.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Min Wen, Shujuan Lu, Chaogang Fan, Kai Shen, Shaohui Lin, Qinmin Pan
Summary: A palladium(II)-coordinated covalent organic framework (Pd(II)@COF) was synthesized mechanochemically and demonstrated as a catalyst for conjugate addition reactions. The catalyst showed good recyclability with >80% yields in the first 4 cycles, broadening the application of COFs in catalysis and providing a new option for Pd(II)-catalysis.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Sheng Zhang, Wenchao Gao, Jianxue Shi, Jingjing Li, Fengyi Li, Yating Liang, Xuan Zhan, Man-Bo Li
Summary: An umpolung addition of dicyanobenzene to alpha,beta-unsaturated alkenes has been developed using an electroreductive strategy. The electrochemical protocol is compatible with challenging substrates, and good regioselectivities are observed in the reaction. The synthetic utility of this electrochemical approach is demonstrated by direct functionalization of two compounds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Jia-Ju Tao, Jia-Dong Tang, Tao Hong, Jia-Wen Ye, Jia-Yu Chen, Chunsong Xie, Zibin Zhang, Shijun Li
Summary: A new class of aza-crown ether-derived chiral BINOL catalysts showed higher enantioselectivity in the asymmetric Michael addition, although the host-guest complexation of alkali ions by the aza-crown ethers did not enhance the catalysis effectiveness. Chiral gamma,delta-unsaturated ketones were obtained in good enantioselectivities (81-95% ees) under mediation of the aza-crown ether-derived chiral BINOL and in the presence of a magnesium salt.
Article
Chemistry, Organic
Yu-Jie Li, De-Guang Liu, Jin-Hu Ren, Tian-Jun Gong, Yao Fu
Summary: Photocatalytic oxidation is a widely used method in organic synthesis, and has applications in both academia and industry. In this study, we developed a blue light-induced alkylation-oxidation tandem reaction for the synthesis of diverse ketones. This reaction shows excellent functional group compatibility and can be used with a variety of radical precursors.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Daniel Rozsar, Alistair J. M. Farley, Iain McLauchlan, Benjamin D. A. Shennan, Ken Yamazaki, Darren J. Dixon
Summary: This article describes the enantioselective intermolecular conjugate addition of nitroalkanes to unactivated alpha,beta-unsaturated esters catalyzed by a bifunctional iminophosphorane (BIMP) superbase. It provides a straightforward approach to the synthesis of pharmaceutically relevant enantioenriched gamma-nitroesters with unprecedented selectivity. The methodology demonstrates broad substrate scope and has been successfully applied on a gram scale with reduced catalyst loading, allowing for catalyst recovery.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Guiying Xiao, Chaochao Xie, Qianling Guo, Guofu Zi, Guohua Hou, Yuping Huang
Summary: A highly enantioselective Ni-catalyzed hydrogenation reaction has been successfully developed for the synthesis of chiral carboxylic acids and other organic compounds, with significant applications in pharmaceuticals and materials science.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Lu Zhao, En-Ze Yao, Guo-Li Chai, Shi-Yu Ma, Junbiao Chang
Summary: In this study, the (R)-3,3'-Br-2-BINOL-catalyzed enantioselective conjugate addition of organic boronic acids to beta,gamma-unsaturated alpha-ketoesters was achieved with moderate to high yields and moderate to excellent enantioselectivities (up to 99% ee). The catalytic system displayed characteristics of mild reaction conditions, high efficiency, and tolerance to alkenylboronic acids and heteroarylboronic acids.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Applied
Sushovan Paladhi, Jin Hyun Park, Barnali Jana, Han Yong Bae, Choong Eui Song
Summary: This review summarizes recent advances in the construction of all-carbon quaternary or hetero-carbon quaternary stereocenters via metal-catalyzed and organocatalyzed asymmetric conjugate addition to β,β-disubstituted nitroalkenes, focusing on the scope, applications, and mechanisms of these reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Hu Tian, Hong-Ming Zhang, Liang Yin
Summary: In this article, a copper(I)-catalyzed asymmetric conjugate addition/protonation with selenols and alpha-substituted alpha,beta-unsaturated thioamides is described, which produces a series of chiral selenides with high to excellent enantioselectivity. The reaction shows a broad substrate scope for both selenols and alpha-substituted alpha,beta-unsaturated thioamides. The catalytic system is also successfully used for asymmetric selenation of beta-substituted alpha,beta-unsaturated thioamides. A [Cu-(R,R-P)-TANIAPHOS]-SePh species is identified by Se-77 NMR spectra, with a chemical shift at delta 462 ppm. Furthermore, a {[Cu-(R)-TOL-BINAP]-SePh}(2) species is characterized by X-ray analysis, confirming the formation of Cu-Se bond in the reaction. Finally, the straightforward transformations of the thioamide group to amine and thioester are demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Giulia Brufani, Federica Valentini, Gabriele Rossini, Luigi Carpisassi, Daniela Lanari, Luigi Vaccaro
Summary: We report a multi-step flow protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles starting from alpha,beta-unsaturated carbonyls. The best results were obtained using a sequential combination of two flow reactors: one packed with a tailor-made POLITAG-F organocatalytic system and a copper tube apparatus. The use of aqueous acetonitrile azeotrope led to excellent catalytic performances in both processes while minimizing waste.
Article
Chemistry, Multidisciplinary
Liang Tang, Yicong Luo, Cheng Sheng, Fang Xie, Wanbin Zhang
Summary: This article reports the efficient kinetic resolution of gamma-substituted alpha,beta-unsaturated gamma-lactams via a Cu-catalyzed asymmetric boron conjugate addition, which leads to the synthesis of chiral beta-hydroxy-gamma-lactams with beta,gamma-stereogenic carbon centers. The method is successful with a wide range of substrates and exhibits versatile transformations and synthetic utility in biologically active molecules. Mechanistic studies indicate that a Lewis acid Cu-I-catalyzed mechanism is the likely pathway in the catalytic reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Daniel Rozsar, Michele Formica, Ken Yamazaki, Trevor A. Hamlin, Darren J. Dixon
Summary: This paper describes a metal-free catalytic intermolecular enantioselective Michael addition to unactivated alpha,beta-unsaturated amides. Consistently high enantiomeric excesses and yields were obtained under mild reaction conditions, using a novel squaramide-based bifunctional iminophosphorane catalyst. Computational analysis revealed the origin of the high enantiofacial selectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Shuai Huang, Gao-Peng Zhang, Yang-Jie Jiang, Fei-Le Yu, Chang-Hua Ding, Xue-Long Hou
Summary: This article presents a facile and efficient method for constructing vicinal tertiary and quaternary chiral carbon centers in synthetic chemistry. By using Kundig-type chiral N-heterocyclic carbene as the ligand, the reaction between Pd-catalyzed umpolung asymmetric allylic alkylation of hydrazones and monosubstituted allyl reagents achieves high yields and high selectivities.
CHEMICAL COMMUNICATIONS
(2022)
Article
Engineering, Environmental
Yongqing Ren, Hao Li, Jinxin Liu, Mengdie Zhou, Jianming Pan
Summary: In this study, a crescent-shaped micromotor sorbent with sulfonic group was prepared for efficient extraction and enrichment of lithium ions. CSMSs showed self-propelled and rapid mixing capabilities, demonstrating excellent adsorption performance. This synthesis method provides a new approach for the preparation of functional and Janus self-propelled micromotors.
JOURNAL OF HAZARDOUS MATERIALS
(2022)
Article
Chemistry, Organic
Juan Wang, Yun-Fan Li, Juan Du, Shuai Huang, Chang-Hua Ding, Henry N. C. Wong, Xue-Long Hou
Summary: Alkynyl esters can undergo palladium-catalyzed asymmetric (3 + 2) cycloaddition with vinyl epoxides, leading to the formation of chiral dihydrofurans with high yields and high enantiomeric excess values when a chiral benzylic substituted P,N-ligand is used. The synthetic method has also been demonstrated for the synthesis of 2,3-cis-tetrahydrofuran.
Article
Engineering, Chemical
Mengdie Zhou, Pan Wang, Yulin Song, Hao Li, Jianquan Luo, Jianming Pan
Summary: In this study, Janus single hole hollow nanoparticles (J-HNPs) encapsulating molecularly imprinted polymers (MIPs) were successfully designed and applied for the effective and selective separation of 2'-deoxyadenosine (dA) in complex biological samples. The hybrid sorbent showed fast adsorption equilibrium for dA within 40 minutes and maintained 88% of the initial capacity after four consecutive adsorption-desorption cycles, demonstrating excellent recognition ability.
SEPARATION AND PURIFICATION TECHNOLOGY
(2022)
Article
Engineering, Environmental
Danqing Shen, Yulin Song, Xuping Chen, Yongquan Zhou, Hao Li, Jianming Pan
Summary: This study reports a method of efficiently removing fluoride from water using ultrafine zirconium oxide-based composite sorbents. The composite sorbents exhibit outstanding defluorination capacity and quick adsorption rate, making them highly promising for the treatment of fluoride pollution in wastewater.
CHEMICAL ENGINEERING JOURNAL
(2022)
Article
Chemistry, Physical
Hao Li, Fan Wu, Yang Pan, Yuting Zhang, Roser Pleixats, Jianming Pan
Summary: With the rapid development of the automobile industry and increasingly strict regulations on automobile exhaust emissions, the demand for palladium will increase as the production of waste purification catalysts for automobile exhaust increases. Recycling waste three-way catalysts is an important way to obtain palladium resources, but obtaining highly selective adsorbents for palladium is still a challenge. In this study, two different Pd2+ selective composite adsorbents were successfully fabricated and characterized. The experimental results showed that both adsorbents exhibited high selectivity towards Pd2+ and remained stable during cyclic adsorption-desorption runs.
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS
(2022)
Article
Engineering, Environmental
Xue Bai, Jing Tang, Hao Li, Jianming Pan
Summary: This study presents a convenient design of amidoxime (AO)-functionalized hydrogel sorbent with interconnected pores for fast and selective uranium extraction. The newly developed sorbent exhibits an open-cell structure with interconnecting pores and demonstrates superior uranium adsorption capacity and uptake rate compared to previously reported hydrogel sorbents. The sorbent also shows excellent recyclability and removal efficiency in the presence of competitive ions. Furthermore, the study reveals the synergistic effect of carboxylates from GelMA in enhancing uranium uptake through charge interaction. Overall, this work provides a new strategy for preparing stable macroporous hydrogel sorbents and offers insights into uranium recovery from aqueous solutions.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Engineering, Environmental
Fan Wu, Hao Li, Yang Pan, Yonghui Sun, Jianming Pan
Summary: A bioinspired magnetic nano stirring rod with dual mesopores and 8-aminoquinoline was proposed for quick and selective recovery of palladium (Pd) from highly acidic sample solutions. The rod exhibited enhanced adsorption capacity and kinetics, and showed excellent selectivity towards Pd(II) compared to coexisting ions. The adsorption mechanisms were ion exchange and chelation. The rod also demonstrated stable adsorption capacity after multiple adsorption-desorption cycles, and exhibited high adsorption capacity from leachate of abandoned high-voltage patch capacitor.
JOURNAL OF HAZARDOUS MATERIALS
(2023)
Article
Engineering, Chemical
Fan Wu, Hao Li, Yang Pan, Yingjia Wang, Yonghui Sun, Jianming Pan
Summary: This study reports a modified magnetic nano stirring robot, which can efficiently and rapidly recover precious metal palladium from waste resources. The robot has ultra-high solid-liquid separation efficiency and self-stirring ability to accelerate mass transfer rate during adsorption. Adsorption experiments show fast kinetics, reaching 10.97 mg g-1 in 20 min, which is 85.87% of the equilibrium adsorption capacity. The robot also demonstrates excellent adsorption selectivity for Pd(II) based on selectivity parameters. Furthermore, it has been proven to be effective for palladium recovery in actual samples and as a catalyst for the Suzuki-Miyaura cross-coupling reaction.
SEPARATION AND PURIFICATION TECHNOLOGY
(2023)
Article
Engineering, Chemical
Wenqing Wang, Hao Li, Xinmin Ma, Jianming Pan
Summary: In this research, sol-gel method and emulsion template approach were combined to construct silica-shell microcapsules filled with ionic liquid. Surface-functionalized silica-shell encapsulated ionic liquid microcapsules were successfully formulated. These microcapsules showed high adsorption properties and excellent regeneration performance for removing 3,4,5-trichlorophenol.
SEPARATION AND PURIFICATION TECHNOLOGY
(2023)
Article
Engineering, Chemical
Peiwen Zhu, Shushun Luo, Hao Li, Jianming Pan
Summary: Iron oxide and mesoporous silica are combined to create magnetic-mesoporous nanoparticles, which have excellent adsorption kinetics and selective extraction capabilities for uranium. The anisotropic Janus nanoparticle consists of one AO functionalized mesoporous silica nanorods and a carbon coated Fe3O4 nanoparticle, and it shows high surface area and saturation magnetization. The nanoparticles can rapidly adsorb uranyl ions and be easily collected under a magnetic field.
SEPARATION AND PURIFICATION TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Yang Pan, Ruirui Liu, Liting Luo, Zhipeng Song, Jianming Pan, Hao Li
Summary: An intelligent magnetic nanorobot was developed for rapid and selective gold stripping from leaching solutions from e-waste leachates. It exhibited excellent adsorption capacity, selectivity, stability, and recycling ability. Additionally, it showed potential for industrial-scale treatment of e-waste and future development of sustainable waste utilization systems.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Physical
Fan Wu, Hao Li, Jing Tang, Abdul Haleem, Jianming Pan
Summary: This study has developed a new sorbent, m-CNTs@H-PDA-AO, for efficient extraction of uranium from seawater. By utilizing the wettability of the magnetized nanomaterial surface, the growth of nanobubble templates was regulated, leading to the successful integration of hollow polymer nanospheres onto the surface of magnetic carbon nanotubes. The sorbent showed rapid adsorption kinetics, good selectivity for uranium, and stability after multiple cycles of adsorption and desorption.
JOURNAL OF MATERIALS CHEMISTRY A
(2023)
Article
Chemistry, Multidisciplinary
Hao Li, Yang Pan, Fan Wu, Yingying Zhou, Jianming Pan
Summary: There is an urgent need for a method to selectively capture and separate gold from secondary resources to combat the depletion of gold resources and reduce the environmental impact. In this study, a highly selective and redox active adsorbent was prepared for the recycling of gold from e-waste. The adsorbent showed enhanced adsorption capacity and kinetics, as well as excellent selectivity and recovery rates, indicating its great potential for gold recycling from complex e-waste leaching solution.
Article
Engineering, Environmental
Mengdie Zhou, Guang Yang, Xiaohua Tian, Songlin Xue, Hao Li, Jianming Pan
Summary: In this study, hybrid polymer nanosheets were prepared through a one-step Pickering oil-in-water-in-oil double emulsion (O/W/O) system stabilized by palmitic chloride modified halloysite nanotubes. The functional hybrid polymer nanosheets were achieved by covalently immobilizing amino ethyl benzo-12-crown ether onto the polymer nanosheets. These hybrid polymer nanosheets exhibited both cured and nanosheet-like structure, and showed excellent selectivity towards lithium ion (Li+). The material also demonstrated good regeneration and mechanical properties, making it a promising sorbent for selective separation.
JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING
(2022)
