Article
Chemistry, Multidisciplinary
Shentong Xie, Yuqing Yin, Ya Wang, Jiannan Wang, Xiaoqian He, Ruopeng Bai, Renyi Shi
Summary: The electroreductive cross-electrophile coupling is a powerful, green, and efficient method for constructing challenging C-C bonds, which has attracted increasing attention from organic chemists. Most of the previous works focus on direct two-electrophile cross-coupling. In this work, a nickel-catalyzed three-electrophile electroreductive cross-electrophile coupling has been developed, offering a direct and convergent synthesis to target molecules from easily available and cheap substrates under mild conditions.
Article
Chemistry, Organic
Le-Cheng Wang, Nai-Xian Sun, Chang-Sheng Wang, Kai Guo, Xiao-Feng Wu
Summary: The direct concurrent installation of amide and ester groups across olefin motifs is a powerful and promising functionalization tool in organic chemistry. Here, a ligand-free cobalt-catalyzed four-component radical relay carbonylative difunctionalization of ethylene for the synthesis of 4-oxobutanoates has been developed, providing a highly atom-economical approach for the production of valuable C4 building blocks.
Article
Biochemistry & Molecular Biology
Sami Chniti, Laszlo Kollar, Attila Benyei, Attila Takacs
Summary: This research investigates the aminocarbonylation reaction of 6-iodoquinoline, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. The study shows that reaction conditions significantly influence the formation of amides and ketoamides, and by optimizing the conditions, selective synthesis of the desired products can be achieved.
Article
Chemistry, Organic
Hui-Qing Geng, Xiao-Feng Wu
Summary: A copper-catalyzed alkoxycarbonylation transformation of unactivated alkyl iodides has been developed to produce tert-butyl esters in good yields. Other types of aliphatic esters can also be obtained in moderated yields with the addition of extra alcohols. Both primary and secondary alkyl alcohols can react successfully in this reaction.
Article
Chemistry, Organic
Yiwen Zhu, Binghu Guo, Shenkui Gao, Jun Ying, Xiao-Feng Wu
Summary: A new cobalt-catalyzed carbonylative synthesis of free (NH)-tetrahydro-beta-carbolinones from tryptamine derivatives has been developed using a traceless directing group strategy. The reaction produced a variety of free (NH)-tetrahydro-beta-carbolinones in good yields. Moreover, late-stage modifications of several bioactive molecules could also be achieved.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Song-Zhou Cai, Rongrong Yu, Can Li, Hongyu Zhong, Xichang Dong, Bill Morandi, Juntao Ye, Xianjie Fang
Summary: Hydrothiocarbonylation of olefins using carbon monoxide and thiols is a powerful method to synthesize thioesters. However, transition-metal-catalyzed asymmetric thiocarbonylation, particularly with earth abundant metals, is rarely reported. In this study, a nickel-catalyzed enantioselective hydrothiocarbonylation of cyclopropenes was developed for the synthesis of functionalized thioesters with high stereoselectivity.
Article
Chemistry, Organic
Fanni Bede, Laszlo Kollar, Nandor Lambert, Peter Huszthy, Peter Pongracz
Summary: Palladium-catalyzed hydroaminocarbonylation reactions of olefins using aliphatic amines were successfully performed under carbon monoxide atmosphere. The targeted amides were synthesized in moderate to good isolated yields without the need for acidic additives. The effect of chiral diphosphines on product distribution, including chemo-, regio-, and enantioselectivities, was also investigated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Xudong Fang, Fuli Wen, Xiangnong Ding, Hanbang Liu, Zhiyang Chen, Zhaopeng Liu, Hongchao Liu, Wenliang Zhu, Zhongmin Liu
Summary: This study proposes a strategy for efficiently converting methane to acetic acid using CH3Cl as an intermediate. The pyridine-pretreated MOR catalyst achieves high selectivity of acetic acid and methyl acetate under moderate conditions. Water, conventionally detrimental to carbonylation reaction, was found to be conducive in this reaction system. This strategy provides a new approach for the highly efficient utilization of methane to oxygenates under mild conditions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Ida Ziccarelli, Lucia Veltri, Tommaso Prestia, Roberta Amuso, Maria A. Chiacchio, Raffaella Mancuso, Bartolo Gabriele
Summary: Unreported 2-(4-acylfuran-2-yl)acetamides were selectively synthesized in fair to good yields (54-81%) over 19 examples through a mild catalytic process involving Csp-H activation, 5-exo-dig O-cyclization, and aromative isomerization.
Article
Chemistry, Multidisciplinary
Takanari Matsutani, Kotaro Aoyama, Toshiyuki Moriuchi
Summary: In this study, a commercially available and easy-to-handle oxovanadium(V) compound is shown to be an efficient catalyst for the synthesis of ureas from disilylamines and carbon dioxide under ambient pressure. The catalytic activation of carbon dioxide occurs without any additives, demonstrating a wide range of applicable substrates and easy scalability. Furthermore, this catalytic system can be used for the synthesis of unsymmetric ureas and chiral urea while retaining chirality.
Article
Chemistry, Organic
Yan-Hua Zhao, Xing-Wei Gu, Xiao-Feng Wu
Summary: This paper reports a ligand-free visible-light-induced manganese-catalyzed carbonylation reaction for the synthesis of various amides. The method offers advantages such as low cost and low toxicity, and can proceed effectively at ambient temperature and pressure.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Wenlong Ren, Mingzhou Wang, Jianqiong Guo, Jintao Zhou, Jianxiao Chu, Yuan Shi, Yian Shi
Summary: A regioselective Pd-catalyzed hydrocarboxylation of terminal olefins with HCOOH is described. A wide variety of branched carboxylic acids can be obtained easily under mild reaction conditions with high regioselectivities. The operation of the reaction is simple and does not require handling toxic CO. The ligand and LiCl play important roles in reaction reactivity and selectivity.
Article
Chemistry, Organic
Junjie Huang, Baihui Liang, Xiuwen Chen, Yifu Liu, Yawen Li, Jingwen Liang, Weidong Zhu, Xiaodong Tang, Yibiao Li, Zhongzhi Zhu
Summary: A simple and practical method for alpha-ketoamide synthesis via a decarboxylative strategy of isocyanates with alpha-oxocarboxylic acids has been described. The reaction proceeds at room temperature under mild conditions without the need for an oxidant or an additive, showing good substrate scope and functional compatibility. The applicability of this method was further demonstrated by the synthesis of various bioactive molecules and different application examples through a two-step one-pot operation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Jun Gu, Fengyue Zhao, K. N. Houk, Qianqian Lu, Fang Liu
Summary: The palladium-catalyzed annulation of o-haloanilines with CO and CO2 for the synthesis of isatoic anhydrides was studied using DFT calculations. The results show that carbonylation precedes carboxylation in the mechanism, and the base plays a crucial role in facilitating the reaction. The study demonstrates the perfect cooperation of CO and CO2 in constructing an anhydride moiety for o-haloanilines.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Bo Zhang, Wei Deng, Zheng-Yang Xu
Summary: In this article, a method for the synthesis of N,N'-diphenyl urea and N-phenyl carbamate by transition-metal-catalyzed carbonylation is introduced. The reaction proceeds through sequential amine C-H bond activation, carbonyl insertion, nucleophilic attack, and oxidation. Moreover, the indenones obtained with Mo(CO)6 as a CO surrogate can be functionalized to form synthetic useful derivatives.
Article
Chemistry, Organic
Jiwei Wu, Kejun Jin, Ruiyou Wang, Xingyu Wang, Xiaoxiao Yu, Liangcheng Zhong, Jianguo Liu
Summary: An efficient electrochemical method has been developed for the synthesis of 4-quinolones via intramolecular C-H/C-H cross-coupling under metal- and external oxidant-free conditions. This method provides a simple and efficient route to construct useful 4-quinolone derivatives in moderate to good yields.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Yongli Li, Huamin Wang, Zhuning Wang, Hesham Alhumade, Zhiliang Huang, Aiwen Lei
Summary: This article describes a method for selectively activating C(sp(3))-S bonds, which is achieved through a radical-mediated electrochemical strategy for the synthesis of valuable disulfides from thioethers. The method features mild reaction conditions and excellent chemoselectivity.
Article
Chemistry, Organic
Hung-Chi Chen, Chenggang Wan, Wan-Hsuan Shih, Ciao-Ying Kao, Haoyang Jiang, Yue Weng, Chien-Wei Chiang
Summary: Electrochemical synthesis in chemical biology offers a milder and environmentally friendly approach to construct novel bioconjugated systems. This study demonstrates an indirect electrochemical strategy for trifluoromethylation of tryptophan residues, enabling the production of fluorinated peptides characterized by F-19-NMR. Mechanistic studies suggest that the transformation proceeds through ferrocene-mediated indirect electrolysis, providing a new toolkit for trifluoromethylation of peptides containing tryptophan.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jianguo Hu, Shengchun Wang, Bin Li, Aiwen Lei
Summary: We report a protocol for constructing tetrahydroquinolines from bulk chemicals (alkenes and anilines) induced by K2S2O8. The method exhibits operational simplicity, wide scope, mild conditions, and a transition-metal-free system.
Article
Chemistry, Organic
Chang-Ming You, Cheng Huang, Sheng Tang, Peng Xiao, Shengchun Wang, Zhenhong Wei, Aiwen Lei, Hu Cai
Summary: Direct N-allylation of azoles with hydrogen evolution has been achieved by the synergistic combination of organic photocatalysis and cobalt catalysis. This protocol eliminates the need for stoichiometric oxidants and prefunctionalization of alkenes, and produces hydrogen (H2) as a byproduct. The transformation highlights high step and atom economy, high efficiency, and broad functional group tolerance, opening up a pathway for valuable C-N bond formation in heterocyclic chemistry.
Article
Multidisciplinary Sciences
Dongfeng Yang, Zhipeng Guan, Yanan Peng, Shuxiang Zhu, Pengjie Wang, Zhiliang Huang, Hesham Alhumade, Dong Gu, Hong Yi, Aiwen Lei
Summary: By electrochemical oxidative difunctionalization, the authors achieved functionalization of diazo compounds with two different nucleophiles. This method allows the synthesis of structurally diverse heteroatom-containing compounds, which are difficult to access by traditional methods, and display important synthetic applications. The reaction conditions are mild, exhibiting excellent functional group tolerance and efficiency for large-scale synthesis.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Jun Yang, Pan Zhang, Zeyuan Shen, Yi Zhou, Zhi-Xiang Yu
Summary: We propose an endo-oxidative cyclometallation (endo-OCM) reaction as a new reaction mode, which can provide a new concept for chemistry and the design of other reactions. We report a Rh(I)-catalyzed intramolecular [4 + 3] cycloaddition reaction, which efficiently synthesizes 5/7-fused bicyclic skeletons with a bridgehead ethyl substituent. Quantum chemical calculations have been carried out to analyze factors affecting the competition of exo-OCM and endo-OCM.
Editorial Material
Chemistry, Physical
Shengchun Wang, Aiwen Lei
Summary: A detailed mechanistic picture of electron transfer in polypyridine nickel systems has been reported, providing an answer to the challenging puzzle of electron transfer in these complexes.
Review
Chemistry, Multidisciplinary
Li Zeng, Jianxing Wang, Daoxin Wang, Hong Yi, Aiwen Lei
Summary: Organic electrosynthesis using alternating current (AC) is still in its early stages due to the lack of a comprehensive theoretical framework. This article provides an overview of recent advancements in AC-driven organic transformations and explores the differences between DC and AC electrolytic methodologies based on their physical principles. These differences include the prevention of metal catalyst deposition, precise modulation of oxidation and reduction intensities, and mitigation of mass transfer processes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chien-Wei Chiang, Hung-Li Li, Ting-Jun Lin, Hung-Chi Chen, Yi-Hsien Chou, Chih-Ju Chou
Summary: This study reported a strategy that combines electrochemical synthesis and photoredox catalysis for the efficient synthesis of imines. The approach showed high versatility in producing symmetric and unsymmetric imines by exploring different substituents on the benzene ring. Specifically, the method was successfully applied to modify N-terminal phenylalanine residues, demonstrating its potential in chemical biology applications. This technique provides a convenient and efficient platform for imine synthesis with broad implications in drug development and organic synthesis.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Jiwei Wu, Yuting Zhang, Jingyi Yang, Lingxiang Yu, Shaoqing Zhang, Jie Zhou, Zirong Li, Xiaolan Xu, Huajian Xu
Summary: A novel method for the synthesis of formamides through the decarboxylative N-formylation of amines with glyoxylic acid has been developed. This method provides an efficient protocol for the synthesis of various formamides with moderate to excellent yields, and it can accommodate a wide range of functional groups under metal free and base free conditions. Moreover, the large-scale experiments and high chemoselectivity have shown great potential application of this strategy.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Xingchen Liu, Haohua Chen, Dali Yang, Binjing Hu, Ying Hu, Shengchun Wang, Yu Lan, Aiwen Lei, Jie Li
Summary: A multicomponent sulfonylation reaction using sulfonyl chlorides and OPiv-supported organozinc reagents was achieved via cobalt-catalyzed alkene difunctionalizations. Anion-coordination played a critical role in modifying the reactivity and chemical properties of organozinc reagents. The OPiv-coordination resulted in the lower reducibility of arylzinc pivalates, allowing for the in situ formation of catalytically relevant Co(I) species as the active catalyst in carbosulfonylation reactions.
Article
Chemistry, Multidisciplinary
Chien-Wei Chiang, Kai-Wun Jhang, Jeng-Lung Chen, Liang-Ching Hsu, Wei-Hsiang Huang, Hung-Chi Chen, Ting-Jun Lin, Ci-Yang Sun, Yu-Ning Li
Summary: In this study, a bioinspired {Co(NO)(2)}(10) complex 1 was developed for S-nitrosation of Cys residues. By incorporating a ferrocenyl group, the nitrosation reaction was fine-tuned using the redox ability of Cys residues. Complex 1 was synthesized and characterized, showing its NO translation reactivity. Moreover, complex 1 successfully converted Cys into S-nitrosocysteine (Cys-SNO), as confirmed by UV-Vis, IR, and XAS spectroscopy. This study presents a promising approach for further exploration in the modification of Cys-containing peptides.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jiwei Wu, Haowen Shi, Jianguo Liu, Ruiyou Wang, Jie Zhou, Xiao-Lan Xu, Hua-Jian Xu
Summary: We have developed a facile and novel electrochemical oxidative C(sp(3))-H/O-H cross-coupling method, which enables the synthesis of various useful α-acyloxyketones with moderate to excellent yields under transition metal- and oxidant-free conditions. A wide range of carboxylic acids including aromatic and aliphatic acids, as well as ketones, are compatible with this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Chien-Wei Chiang, Yi-Hsien Chou, Chih-Hui Chou, Hung-Chi Chen, Jeng-Lung Chen, Liang-Ching Hsu, Wei-Hsiang Huang, Hung-Li Li, Yu-Hao Liu
Summary: This study investigates the mechanism of alcohol oxidation using a ferrocene-conjugated copper complex, offering valuable insights and potential for developing efficient and eco-friendly catalysts for chemical synthesis.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2023)
