Article
Chemistry, Multidisciplinary
Hsuan-Hung Liao, Shao-Chi Lee, Hsin Kao, Yu-Ling Hsu, Che-Ming Hsu, Yong-Ting Tsao, Shinje Minoza, Li-Yun Li, Zong-Nan Tsai, Kuei-Chen Chang, Cheng-Ku Cheng, Cheng-Lin Chan, Yi-Sian Chien, Cheng-chau Chiu
Summary: This article presents a new method for synthesizing perfluoroaryl sulfides, which can be conducted at ambient conditions or as industrial processes, with a wide tolerance for various functional groups. The reaction mechanism involves a nucleophilic attack of a thiol group on an electron-poor aromatic ring, with a predicted stepwise or concerted mechanism.
CELL REPORTS PHYSICAL SCIENCE
(2022)
Article
Chemistry, Inorganic & Nuclear
Ka Yee Yee, Man Pan Leung, Man Ho Tse, Pui Ying Choy, Fuk Yee Kwong
Summary: This paper presents the first general examples of palladium-catalyzed direct C-H olefination of polyfluoroarenes using alkenyl tosylates as electrophilic coupling partners. Good-to-excellent yields of olefinated polyfluoroarenes can be obtained by employing the Pd/L1 catalyst system. The reaction exhibits good structural and functional compatibility, and particularly smooth reactivity for steric demanding and heterocyclic alkenyl tosylates. It can be practically performed on a gram-scale without significant loss of product yields.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ye Yuan, Muliang Zhang, Xiaodong Tang, Jared L. Piper, Zhi-Hui Peng, Jun-An Ma, Jie Wu, Fa-Guang Zhang
Summary: We have developed a photoredox platform that utilizes sulfinate as a radical-relay precursor and a sacrificial nucleofuge, allowing for the construction of styrenyl polyfluoro (hetero)arenes with branch selectivity. This protocol combines photoredox catalysis, radical-radical coupling, and an elimination process in a one-pot operation, providing a mild and efficient method to access polyfluoro (hetero)aryl derivatives of natural products and drugs.
Article
Chemistry, Physical
Jin Zhang, Jiale Liu, Xiaogang Wang, Xinkan Yang, Yangmin Ma, Ran Fang, Qun Zhao, Michal Szostak
Summary: This study reports a ruthenium-catalyzed site-selective arylation of C-F bonds in polyfluoroarenes, enabling the synthesis of complex multifluorinated biaryls. This approach exhibits broad scope and functional group tolerance, allowing for the preparation of polyfluorinated ligands, heterocycles, pharmaceuticals, and porphyrin analogues.
Article
Chemistry, Multidisciplinary
Nurbey Gulia, Jaroslaw Fornalski, Adrianna Gumienna, Malgorzata Ambroziak, Slawomir Szafert
Summary: This study reports a method of palladium-catalyzed C-H arylation assisted with a 3,4,4-trimethylpyrazol-5-on directing group, which selectively provides mono- and di-ortho-arylated products. The steric hindrance between the directing group and the already introduced aryl substituent enables control of mono- vs. diarylation selectivity by the reaction temperature. A series of monosubstituted and disubstituted derivatives were obtained in good yields. In addition, a one-pot procedure for unsymmetrical double-arylation to give corresponding products was developed, and the synthesis and X-ray study of intermediate palladium metallacycles were conducted. The decarboxylative cleavage of the pyrazolone directing group under mild conditions gave synthetically useful hydrazones. Overall, this solution provides an alternative synthetic pathway for ortho arylated derivatives of arylhydrazines.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Longlong Xi, Liting Du, Zhuangzhi Shi
Summary: A nickel-catalyzed reductive cross-coupling reaction has been reported for the synthesis of substituted fluoroarenes through chelation-assisted C-F activation of polyfluoroarenes and alkyl electrophiles. The method shows excellent regioselectivity and can be applied to various primary and secondary alkyl (pseudo)halides.
CHINESE CHEMICAL LETTERS
(2022)
Article
Multidisciplinary Sciences
Bingnan Du, Chun-Ming Chan, Pui-Yiu Lee, Leong-Hung Cheung, Xin Xu, Zhenyang Lin, Wing-Yiu Yu
Summary: The authors developed diverse 2,2-difluorovinyl benzoates as versatile building blocks for modular synthesis of gem-difluoroenol ethers and gem-difluoroalkenes using nickel-catalyzed cross coupling. The method allows for late-stage functionalization of multifunctionalized bioactive molecules due to the diversity of the building blocks and excellent functional group tolerance.
NATURE COMMUNICATIONS
(2021)
Article
Engineering, Environmental
Min Long, Juan Donoso, Manav Bhati, Welman C. Elias, Kimberly N. Heck, Yi-Hao Luo, YenJung Sean Lai, Haiwei Gu, Thomas P. Senftle, Chen Zhou, Michael S. Wong, Bruce E. Rittmann
Summary: The study showed that the removal of perfluorooctanoic acid can be effectively achieved in membrane catalyst-film reactors coated with palladium nanoparticles, maintaining the concentration below the EPA health advisory level for a long period without catalyst loss. Two distinct mechanisms for PFOA removal were identified based on experimental results and theoretical calculations.
ENVIRONMENTAL SCIENCE & TECHNOLOGY
(2021)
Review
Chemistry, Applied
Oleg Y. Lyakin, Dmitry S. Bushmin, Evgenii P. Talsi, Konstantin P. Bryliakov
Summary: This review summarizes the recent advances in homogeneous oxidation of hydrocarbon C(sp(3))-H bonds catalyzed by nickel and palladium complexes, and discusses the correlations between the catalyst structure, ligand properties, catalytic conditions, and catalytic reactivity (efficiency, chemoselectivity, and regioselectivity).
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Zhi-Yu Bo, Si-Shun Yan, Tian-Yu Gao, Lei Song, Chuan-Kun Ran, Yi He, Wei Zhang, Guang-Mei Cao, Da-Gang Yu
Summary: In this study, a novel visible light-driven carboxylation of aryl C-F bonds with CO2 has been reported. The method enables selective carboxylation of strong C(sp(2))-F bonds in various polyfluoroarenes using visible-light photoredox catalysis, providing a facile access to important polyfluoroaryl carboxylic acids.
CHINESE JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Nardana Sivendran, Nico Pirkl, Zhiyong Hu, Angelino Doppiu, Lukas J. Goossen
Summary: Halogen-bridged methylnaphthyl (MeNAP) palladium dimers, presented as versatile Pd precursors, demonstrate excellent catalytic performance by in situ conversion into well-defined monoligated complexes. They show benchmark activities in challenging reactions, enable record-setting yields, and can achieve previously elusive cross-couplings.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Environmental Sciences
Govardhana Reddy Peddiahgari Vasu, Krishna Reddy Motakatla Venkata, Raghava Reddy Kakarla, Kalluri V. S. Ranganath, Tejraj M. Aminabhavi
Summary: This article explores the research of Pd-PEPPSI complexes in recent years, introducing the synthesis of these catalysts and their applications in various reactions. The article also discusses the reusable heterogeneous PdPEPPSI complexes and their catalytic applications, and concludes with a discussion on chiral Pd complexes and their asymmetric transformations.
ENVIRONMENTAL RESEARCH
(2023)
Article
Chemistry, Multidisciplinary
Wei-Chieh Chang, Helena Randel, Thomas Weyhermueller, Alexander A. A. Auer, Christophe Fares, Christophe Werle
Summary: In this study, a cooperative [Rh/P(O)nBu(2)] template was used for the catalytic hydrodefluorination (HDF) of perfluoroarenes under mild reaction conditions. The system showed high chemoselectivity and practicality, even in the presence of electron-donating functionalities and heterocycles. Mechanistic and theoretical studies identified a rhodium(I) dihydride complex as the catalytically relevant species and the crucial role of phosphine oxide as a cooperative fragment. Overall, this work demonstrates the potential of molecular templates for enhancing the reactivity in challenging bond activations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Yuki Kanai, Dorian Mueller-Borges, Herbert Plenio
Summary: The direct arylation of 1,3-benzodioxole and 2,2-difluorobenzo[1,3]dioxole with various aryl bromides yields 4-substituted products in high yields. The nature of the amide and the concentration of the reactants play crucial roles in optimizing reaction conditions. Acetamide acts as a ligand to Pd, not as a solvent, in this reaction.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Fatemeh Ghahramani, Malte Meyer, Shreya Unone, Daniel Janssen-Mueller
Summary: A palladium-catalyzed method for the efficient C-C bond activation of HMF derivatives, enabling their arylation with iodobenzenes, has been developed. Mechanistic studies suggest a decarboxylative mechanism. This strategy offers an efficient and sustainable approach for the synthesis of arylfuran derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Materials Science, Multidisciplinary
Yue Guo, Weidong Song, Qing Liu, Yiming Sun, Zhao Chen, Xin He, Qingguang Zeng, Xingjun Luo, Ruiqing Zhang, Shuti Li
Summary: A filter-free, ultra-narrowband, ultraviolet photodetector based on a porous GaN/MoO3 heterojunction is demonstrated. The optimized porous GaN/MoO3 photodetector exhibits ultra-narrowband ultraviolet photoresponse and a large light-to-dark current ratio, making it promising for optical communication systems.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
Article
Chemistry, Multidisciplinary
Zirong Wang, Fanyuan Meng, Qi Feng, Shengxuan Shi, Langwen Qiu, Guanwei Sun, Zhao Chen, Qingguang Zeng, Weiguo Zhu, Shi-Jian Su
Summary: In this study, efficient green perovskite light-emitting diodes (PeLEDs) were fabricated by optimizing the phase composition and introducing mix-interlayer ligands. The introduction of these ligands greatly suppressed non-radiative recombination, resulting in high photoluminescence quantum yield and narrow emission bandwidth.
FRONTIERS IN CHEMISTRY
(2022)
Article
Engineering, Environmental
Hongyang Zhang, Yingjie Sun, Zhao Chen, Weigao Wang, Qiwei Wang, Shuming Chen, Yuqing Xu, Wai-Yeung Wong
Summary: Solution processing of OLEDs is an attractive approach due to its low cost and accessibility to a variety of materials. This study focuses on the fabrication of high-performance deep red and NIR OLEDs using evaporation and solution processing methods. The devices achieved high maximum external quantum efficiencies and the effects of functional substituents and p-pi conjugation on the optoelectronic properties were investigated. This research provides new insights into developing efficient OLEDs based on Ir(III) complexes.
CHEMICAL ENGINEERING JOURNAL
(2023)
Review
Chemistry, Multidisciplinary
Minqi Zhou, Zhang Feng, Xingang Zhang
Summary: The site-selective modification of amino acids, peptides, and proteins has been an important topic in organic synthesis, medicinal chemistry, and chemical biology. The introduction of fluorine functionalities into these compounds has been a useful approach to alter their properties. Direct fluorination/fluoroalkylation of proteins has gained attention due to the unique properties of fluorine, and recent advances in the synthesis of fluorinated amino acids and peptides have been summarized in this article. Two strategies, based on fluorinated building blocks and direct fluorination/fluoroalkylation, have been discussed, providing powerful tools for selective access to fluorinated amino acids, peptides, and proteins.
CHEMICAL COMMUNICATIONS
(2023)
Article
Engineering, Environmental
Xiaokun Fan, Zhen Mu, Zhao Chen, Yunfeng Zhan, Fanyuan Meng, Yang Li, Guichuan Xing, Wai-Yeung Wong
Summary: An alloyed quantum dot with a core/shell structure of Cd0.194Zn0.806Se0.406S0.594/ZnS was synthesized, which exhibited efficient green emission with high photoluminescence quantum yield (PL QY) and ultra-fast radiative transition rate. The quantum dot also showed potential for applications in light-emitting diodes (LEDs).
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Xin Zeng, Yao Li, Qiao-Qiao Min, Xiao-Song Xue, Xingang Zhang
Summary: The use of metal catalysts in controlling the reactivity of carbenes is widely used in organic synthesis, but the transfer of difluorocarbenes remains a challenge. In this study, isolable copper(I) difluorocarbene complexes were developed and used as catalysts for difluorocarbene transfer reactions. This strategy allows for the modular synthesis of organofluorine compounds and provides access to a variety of difluoromethylene-containing products. Mechanistic studies reveal a nucleophilic addition mechanism involving electrophilic copper(I) difluorocarbenes.
Article
Chemistry, Physical
Na Rao, Yun-Ze Li, Yun-Cheng Luo, Yanxia Zhang, Xingang Zhang
Summary: The nickel-catalyzed multicomponent dicarbofunctionalization of alkenes is a convenient method for synthesizing complex organofluorine compounds, but the catalytic carbofluoroalkylation of electron-deficient alkenes is still underdeveloped. In this study, a nickel-catalyzed three-component aryldifluoroalkylation reaction was reported, which involves the reaction of industry-relevant acrylonitrile and acrylate with arylboronic acids and difluoroalkyl halides. The reaction can be extended to a four-component nickel-catalyzed carbonylation reaction. This modular catalytic synthesis offers synthetic convenience, high functional group tolerance, and the ability to construct complex difluoroalkylated compounds efficiently. The utility of this synthesis has also been demonstrated by transforming the resulting products into fluorinated compounds of medicinal interest.
Article
Chemistry, Multidisciplinary
Yun-Cheng Luo, Ming-Kuan Wang, Ling-Chao Yu, Xingang Zhang
Summary: Here, we report a nickel-catalyzed selective C(sp(2))-F bond alkylation of HFO-1234yf with alkylzinc reagents, resulting in 2-trifluoromethylalkenes that can serve as versatile synthons for diversified transformations. Mechanistic studies reveal that the addition of lithium salt is crucial for promoting the oxidative addition of Ni-0(L-n) to the C-F bond, and less electron-rich N-based ligands exhibit comparable or higher oxidative addition rates compared to electron-rich phosphine ligands.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xiaolong Yang, Shipan Xu, Yan Zhang, Chengyun Zhu, Linsong Cui, Guijiang Zhou, Zhao Chen, Yuanhui Sun
Summary: This study reports two NIR phosphorescent Ir(III) complexes with emission peaks around 730 nm and narrow full width at half maximum of only 43 nm. Pure NIR luminescence can be obtained without a very long emission wavelength, thus overcoming the restriction of the energy gap law and achieving impressively high photoluminescence quantum yield up to 0.70. Moreover, pure NIR organic light-emitting diodes (OLEDs) fabricated by solution-processing method show outstanding device performance with the highest external quantum efficiency of 16.43%, setting a new record for solution-processed NIR-OLEDs based on different emitters.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xue-Ying Zhang, Shi-Ping Sun, Yue-Qian Sang, Xiao-Song Xue, Qiao-Qiao Min, Xingang Zhang
Summary: A palladium-catalyzed reductive difluorocarbene transfer reaction that utilizes chlorodifluoromethane as a precursor has been developed, allowing difluorocarbene to couple with two electrophiles. This new mode of difluorocarbene transfer reaction produces difluoromethylated (hetero)arenes from aryl halides/triflates and proton sources, with high functional group tolerance and synthetic convenience. Mechanistic studies reveal an unexpected Pd-0/II catalytic cycle involved in the reductive difluorocarbene transfer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xing Gao, Xiaoxiao Ren, Wei Deng, Xingang Zhang
Summary: This study reports a copper-catalyzed hydrodifluoroallylation of cyclopropenes and alkenyl boronates with 3,3-difluoroallyl sulfonium salts. The reaction shows high efficiency and stereoselectivity, allowing the synthesis of various gem-difluoroallyl cyclopropanes and borylalkanes under mild reaction conditions. The use of chiral phosphine ligand improves the enantioselectivity of the reaction. This method offers synthetic convenience, high functional group tolerance, and synthetic versatility of the resulting products.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Wenping Ding, Minqi Zhou, Huayu Li, Miao Li, Yanping Qiu, Yu Yin, Lifeng Pan, Wenchao Yang, Yanan Du, Xingang Zhang, Zhijun Tang, Wen Liu
Summary: Modification of organic molecules with fluorine functionalities is a critical approach for developing new pharmaceuticals. In this study, a multienzyme strategy for biocatalytic fluoroalkylation was reported, which involved the use of SAM-dependent methyltransferases and fluorinated SAM cofactors. The strategy demonstrated successful late-stage site-selective fluoroalkylation of the complex molecule vancomycin, with conversions up to 99%.
Article
Chemistry, Physical
Ming-Kuan Wang, Yun-Cheng Luo, Hai-Yang Zhao, Yanxia Zhang, Dawei Zhang, Xingang Zhang
Summary: A cobalt-catalyzed trans-selective arylfluoroalkylation of cyclopentenes has been developed for the efficient synthesis of polysubstituted cyclopentanes. The reaction exhibits broad substrate scope, high functional group tolerance, and synthetic convenience.
Article
Chemistry, Physical
Ling-Chao Yu, Yun-Cheng Luo, Wei Feng, Shu Zhang, Xingang Zhang
Summary: A new organic catholyte material, sodium 2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl-4-yl)-2,2-difluoroacetate (DFTEMPO), is created by introducing a fluorine functionality into 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO), showing higher cell voltage, rate capability, and cycle stability in aqueous redox flow batteries (ARFBs).
JOURNAL OF MATERIALS CHEMISTRY A
(2023)
Article
Chemistry, Multidisciplinary
Hao-Wen Li, Yun-Cheng Luo, Ling-Chao Yu, Xingang Zhang
Summary: A palladium-catalyzed gem-difluoroallylation of propargyl sulfonates with gem-difluoroallylboron has been developed, providing a synthetic route to 3,3-difluoro-skipped 1,5-enynes with high efficiency and regioselectivity. The resulting products can serve as versatile synthons for diversified transformations and have potential applications in medicinal chemistry.
CHEMICAL COMMUNICATIONS
(2023)
