Article
Chemistry, Organic
Mikhail A. Losev, Andrey S. Kozlov, Vladimir B. Kharitonov, Oleg I. Afanasyev, Fedor S. Kliuev, Ludmila A. Bulygina, Natalya S. Khrushcheva, Dmitry A. Loginov, Denis Chusov
Summary: A simple and selective method using carbon monoxide as a reducing agent was developed for the preparation of amides from nitroarenes and carboxylic acids. The protocol does not require non-gaseous additives, simplifying product isolation and saving reducible functional groups.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
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, Physical
Fuli Wen, Jin Zhang, Zhiyang Chen, Ziqiao Zhou, Hongchao Liu, Wenliang Zhu, Zhongmin Liu
Summary: Methane can be effectively activated via carbonylation with CO over Zn/HZSM-5 catalysts under mild conditions, leading to high selectivity to aromatics or ethane. The study demonstrates the potential for transforming methane into value-added chemicals under mild reaction conditions.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Sofiya A. Runikhina, Oleg I. Afanasyev, Ekaterina A. Kuchuk, Dmitry S. Perekalin, Rajenahally V. Jagadeesh, Matthias Beller, Denis Chusov
Summary: Converter gas, a large scale waste product, is usually burned and contributes to greenhouse gas emissions. However, this study shows that it can be utilized as a reducing agent in organic reactions to produce valuable pharmaceuticals and agrochemicals. The gas was used in the synthesis of amide-based drug molecules and classical reductive amination reactions.
Article
Chemistry, Physical
Jian-Xing Xu, Fu-Peng Wu, Xiao-Feng Wu
Summary: In this study, a rhodium-catalyzed reduction of CO using B(2)pin(2) and silane was developed, leading to the formation of versatile H2C(Bpin)(2). This represents the first example of transition metal-catalyzed borylation of CO.
CATALYSIS COMMUNICATIONS
(2021)
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
Chemistry, Multidisciplinary
Oleg L. Eliseev, Tatyana N. Bondarenko, Anastasia D. Churikova, Albert L. Lapidus
Summary: This study reports for the first time the methoxycarbonylation of styrene in the presence of homogeneous Ru catalysts. The combination of available Ru3(CO)12 and a halide source such as [bmim]Br, NaBr, or LiCl results in an active and easy to handle catalytic system for the methoxycarbonylation reaction. The key advantage of this new system over traditional Pd catalysts is its high activity even at a low CO pressure of 5 bar.
MENDELEEV COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Csaba Arvai, Laszlo T. Mika
Summary: This review summarizes the recent applications of alternative solvents in improving the efficiency, safety, and environmental friendliness of carbonylation reactions. The use of water, biomass-based alcohols, ionic liquids, and other alternative solvents can enhance the reaction protocols.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wei Li, Donghao Jiang, Cheng Wang, Li-Jie Cheng
Summary: Transition metal-catalyzed carbonylation reactions provide a direct and atom-economical method for synthesizing carbonyl compounds or their derivatives using CO as a cheap and readily available C1 feedstock. Although carbonylation of less reactive unactivated alkyl electrophiles poses challenges, recent advances using earth-abundant base metals as catalysts have allowed for the synthesis of important and previously difficult-to-access carbonyl compounds or their derivatives.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Physical
Ida Ziccarelli, Raffaella Mancuso, Francesco Giacalone, Carla Calabrese, Valeria La Parola, Alex De Salvo, Nicola Della Ca', Michelangelo Gruttadauria, Bartolo Gabriele
Summary: This article reports the successful heterogenization of the classical PdI(4)(2-)carbonylation catalyst on multi-walled carbon nanotubes. The newly developed heterogeneous catalyst shows good activity and recyclability in the oxidative monoaminocarbonylation reaction, with limited metal contamination in the final organic compounds.
JOURNAL OF CATALYSIS
(2022)
Review
Engineering, Environmental
Jinyong Liu, Jinyu Gao
Summary: This paper discusses the advances, challenges, and opportunities for the research of catalytic reduction of water pollutants. It presents case studies on the development of palladium-based catalysts for the reduction of nitrate, chlorate, and perchlorate. The paper emphasizes the importance of screening and designing catalytic metal sites to achieve new functionalities. It also highlights the convenient catalyst preparation approach and discusses directions that are not immediately necessary or desirable in catalyst research. Finally, it recommends future catalyst development in both fundamental and applied aspects to benefit environmental protection.
FRONTIERS OF ENVIRONMENTAL SCIENCE & ENGINEERING
(2023)
Review
Chemistry, Inorganic & Nuclear
Jian-Xing Xu, Yang Yuan, Xiao-Feng Wu
Summary: In this review, we summarized and discussed the major achievements in transitional metal-catalyzed carbonylative transformations of ethylene. Ethylene hydroformylation, hydroesterification, hydrocarboxylation, hydroaminocarbonylation, dicarbonylation, and multicomponent carbonylation reactions can produce various bulk compounds and fine chemicals, including propanol, alkyl propanoates, succinic diesters, and multifunctionalized C3 compounds.
COORDINATION CHEMISTRY REVIEWS
(2023)
Article
Multidisciplinary Sciences
Zesong Ma, Zhilong Yang, Wenchuan Lai, Qiyou Wang, Yan Qiao, Haolan Tao, Cheng Lian, Min Liu, Chao Ma, Anlian Pan, Hongwen Huang
Summary: This study demonstrates the successful electrochemical reduction of CO2 to multicarbon products in strongly acidic electrolyte by combining the confinement effect and cation effect, showing high Faradaic efficiency, partial current density, and stability. The cation effect is found to play a crucial role in C-C coupling.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
E. G. Chepaikin, G. N. Menchikova, S. I. Pomogailo
Summary: Variation in the nature of components in catalytic systems can influence the selectivity of propane oxidation reactions, leading to different product yields in different systems.
PETROLEUM CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Takashi Kurogi, Keiichi Irifune, Kazuhiko Takai
Summary: Carbon tetrabromide can be reduced with CrBr2 in THF to form a dinuclear carbido complex, which can react with aldehydes, alkenes, and terminal/internal alkynes to generate various products with different reactivities.
Article
Chemistry, Multidisciplinary
Ren-Guan Miao, Weiqi Dai, Xinxin Qi, Xiao-Feng Wu
Summary: C-S bond formation is important in organic synthesis, material science, and medicinal chemistry. This study presents a nickel-catalyzed desulfonative cross-coupling reaction for the synthesis of unsymmetrical thioethers. Using readily available sulfonyl chlorides as both electrophiles and sulfur precursors, various asymmetric thioethers can be synthesized with good yields and functional group tolerance.
CELL REPORTS PHYSICAL SCIENCE
(2023)
Article
Chemistry, Applied
Yue Sun, Sihao Ling, Yubo Duan, Jingxian Li, Zhengkai Chen, Xiao-Feng Wu
Summary: A metal-free approach for constructing 5-trifluoromethyl-1,4-dihydro-1,2,4-triazines has been developed using base-mediated [3+3] cycloaddition. This protocol offers readily available starting materials, mild reaction conditions, a broad substrate scope, high efficiency, good synthetic prospect, and scalability.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Zhi-Peng Bao, Xiao-Feng Wu
Summary: This article develops an efficient and convenient palladium-catalyzed carbonylation reaction for the synthesis of 2-cyano-N-acetamide and 2-cyanoacetate compounds. The reaction proceeds under mild conditions via a radical intermediate, suitable for late-stage functionalization. Gram-scale experiment was successfully performed with low catalyst loading, yielding the target product excellently. Additionally, this transformation can be carried out under atmospheric pressure and provides alternative routes to drug precursors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Zekai Shen, Yong-Wang Huo, Xinxin Qi, Xiao-Feng Wu
Summary: A palladium-catalyzed thiocarbonylation reaction using S-aryl thioformates as the thioester sources was developed for the synthesis of alpha,beta-unsaturated thioesters from vinyltriflates. The reaction proceeded smoothly at low temperature, providing a variety of alpha,beta-unsaturated thioesters in good yields with excellent functional group tolerance. This protocol offers mild reaction conditions, broad substrate scope, and avoids the use of toxic CO gas or odorousthiols, making it a valuable method for the synthesis of alpha,beta-unsaturated thioesters via thioester transfer process.
Article
Chemistry, Organic
Jiajun Zhang, Xiao-Feng Wu
Summary: The development of mild methodology for converting inert C-H bonds to value-added molecules has been an attractive research focus. In this study, versatile palladium-catalyzed carbonylative cross-coupling reactions were reported, which allowed the selective transformation of arenes via C(sp2)-H thianthrenation to produce desired diaryl ketones in good to excellent yields. Diaryl ketones have important applications in antitumor drugs, the agrochemical industry, and synthetic chemistry.
Article
Chemistry, Multidisciplinary
Yan Zheng, Bing-Hong Teng, Youcan Zhang, Xiao-Feng Wu
Summary: In this study, a photo-induced metal-free carbonylation reaction of aryl bromides was developed. The reaction showed good reactivity with alcohol and amine nucleophiles, and a variety of useful aryl esters and amides were synthesized at room temperature in moderate to good yields.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Physical
Chang-Sheng Kuai, Bing-Hong Teng, Yingying Zhao, Xiao-Feng Wu
Summary: A method for the selective deoxygenative and alkoxy carbonylation of alcohols using boronic acids via palladium catalysis has been developed. The choice of activators determines the different selectivities. Carbodiimide activator promotes the formation of ketones through deoxygenative carbonylation, while azo activator leads to ester formation via alkoxy carbonylation. This study expands the substrate scope and allows for the use of base-sensitive boronic acid substrates. It contributes to the understanding and control of chemoselectivity in carbonylation chemistry.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Yang Yuan, Nai-Xian Sun, Chang-Sheng Wang, Kai Guo, Xiao-Feng Wu
Summary: We have developed an efficient method for synthesizing one-carbon-extended alcohols through cobalt-catalyzed hydroxymethylation of alkyl halides using carbon monoxide as the C1 source and cost-effective and environmentally friendly PMHS as the hydride source. This method includes a ligand-free cobalt catalyst and exhibits broad functional group tolerance.
Article
Chemistry, Organic
Shangyuan Wang, Jiajun Zhao, Jun Ying, Xiao-Feng Wu
Summary: This study developed a palladium-catalyzed one-pot two-step radical mediated carbonylative cyclization method to construct polycyclic 3,4-dihydroquinolin-2-(1H)-one scaffolds using perfluoroalkyl iodides and Mo-(CO)(6) with 1,7-enynes. Various polycyclic 3,4-dihydroquinolin-2-(1H)-one derivatives containing perfluoroalkyl and carbonyl units were synthesized with high yields. Moreover, modification of several bioactive molecules was demonstrated using this protocol.
Article
Chemistry, Organic
Guangming Wei, Dongling Zheng, Chen Li, Zhengkai Chen, Xiao-Feng Wu
Summary: Trifluoromethyl-substituted 1,2-dihydroquinoxalines and diimines can be synthesized efficiently through a base-mediated cascade reaction involving the unusual N-N bond cleavage and rearrangement of azo compounds.
Article
Chemistry, Multidisciplinary
Jiajun Zhang, Le-Cheng Wang, Zhi-Peng Bao, Xiao-Feng Wu
Summary: A new reaction for site-selective carbonylation of arenes via C(sp(2))-H thianthrenation under mild conditions has been developed. High yields of desired 1,2-diarylethanones are obtained using low loadings of palladium catalysts. This strategy also allows for late-stage modification of complex molecules, which was previously challenging with similar carbonylative Negishi-type reactions.
Article
Chemistry, Organic
Yubo Duan, Shu-Ning Lu, Zuguang Yang, Zhengkai Chen, Xiao-Feng Wu
Summary: An efficient and straightforward strategy for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones via Rh(iii)-catalyzed C-H activation/annulation of N-carbamoylindoles with CF3-imidoyl sulfoxonium ylides has been achieved. The cascade reaction proceeds through a C-H imidoylmethylation, tautomerization and intramolecular nucleophilic addition sequence, leading to the construction of a wide range of functionalized pyrimidoindolone derivatives in good to excellent yields under redox-neutral conditions.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Han -Jun Ai, Fengqian Zhao, Xiao-Feng Wu
Summary: Iron-catalyzed carbonylation reactions are highly desirable due to their low cost, abundance, and distinct reactivity patterns. In this study, we developed a method for the carbonylative coupling of unactivated alkyl halides with amines, amides, and indoles, resulting in the synthesis of various amides, imides, and N-acyl indoles with high yields and compatibility with other functional groups. Our mechanistic studies revealed that the reaction pathway depends on the substrate, with alkyl iodides proceeding via a radical pathway and alkyl bromides undergoing a two-electron transfer process.
CHINESE JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Hui-Qing Geng, Xiao-Feng Wu
Summary: Cyclopropane is a crucial ring found in various bioactive compounds, especially in clinical medicines. It can be synthesized by reacting olefins with potentially hazardous diazo-derived carbenoids. Carbonylation is a powerful tool for synthesizing carbonylated or carbon-extended compounds. In this study, we describe a straightforward approach for synthesizing beta-boryl cyclopropane derivatives using an inexpensive copper catalyst with CO as the C1 source. This reaction, mediated by an in situ generated carbene intermediate, provided a wide range of cyclopropane-containing organoboron compounds in moderate to good yields.
Review
Chemistry, Multidisciplinary
Zuguang Yang, Guangming Wei, Zhengkai Chen, Xiao-Feng Wu
Summary: Recent research has focused on the direct synthesis of trifluoromethyl-containing heterocycles from TFAICs and its derivatives, such as TFAIHs and TFISYs. Cascade annulation reactions of these synthons with suitable coupling partners have proven to be a powerful tool for constructing a variety of trifluoromethyl-substituted heterocycles. TFAICs and derivatives are advantageous due to their easy availability and handling, relative stability and safety, and high reactivity.
CHEMICAL COMMUNICATIONS
(2023)
