Article
Chemistry, Organic
Jin-He Na, Xiang Liu, Jia-Wen Jing, Jing Wang, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A step-economical and efficient one-pot reaction was developed for the direct cross-coupling of aryl fluorosulfate with aryl bromide. This reaction, conducted at room temperature in THF solvent, does not require the use of preprepared/commercial organometallic reagents. By utilizing nickel catalyst, magnesium turnings, and lithium chloride, the desired biaryls were obtained in moderate to good yields with reasonable functional group compatibility.
Article
Chemistry, Multidisciplinary
Qiaoli Li, Lanting Xu, Dawei Ma
Summary: Direct N-arylation of sulfonamides using a combination of copper and oxalamides (or 4-hydroxypicolinamides) as catalysts is an efficient method. It allows for a wide range of reactions between sulfonamides and (hetero)aryl bromides, and even works well with primary sulfonamides and (hetero)aryl chlorides under the catalysis of Cu2O and a 4-hydroxypicolinamide.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Seoung-Tae Kim, Michael J. Strauss, Albert Cabre, Stephen L. Buchwald
Summary: A new class of anionic ligands for Cu-catalyzed C-N couplings has been developed, which enables efficient amination of aryl bromides under mild conditions. This ligand design increases the electron density on Cu and stabilizes the active anionic CuI complex, leading to enhanced reactivity and a broad substrate scope.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Inorganic & Nuclear
Olmo Lozano-Lavilla, Pablo Gomez-Orellana, Agusti Lledos, Juan A. Casares
Summary: The study found that the mechanism for the formation of homocoupling products when [Cu(bipy)(C6F5)] reacts with Rf-I mainly involves transmetalation from [Cu(bipy)(C6F5)] to Cu(III) intermediates formed in the oxidative addition step. Density functional theory calculations showed that the interaction between these Cu(III) species and the starting Cu(I) complex involves a Cu(I)-Cu(III) electron transfer and the formation of an iodine bridge between the metals.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Fusheng Bie, Xuejing Liu, Han Cao, Yijun Shi, Tongliang Zhou, Michal Szostak, Chengwei Liu
Summary: The Pd-catalyzed double-decarbonylative synthesis of aryl thioethers involves an aryl exchange reaction between amides and thioesters, with amides serving as aryl donors and thioesters as sulfide donors. The use of Pd/Xantphos without any additives promotes aryl exchange by C(O)-N/C(O)-S cleavages, allowing for a wide variety of amides and sulfides to be used in the reaction.
Article
Chemistry, Organic
Yinpeng Wang, Mingming Zhao, Jingke Peng, Hongxia Zheng, Heng-Ying Xiong, Guangwu Zhang
Summary: The first Pd(0)-catalyzed synthesis of aryl-methylene ethers from hydrobenzoxazoles (hydrothiazoles) using dichloromethane (DCM) as the C1 feedstock is reported. This protocol demonstrates a broad substrate scope (38 examples) and wide tolerance to functional groups. The aryl-methylene ether adducts have been successfully coupled with isocyanate to provide bis-iminoisoindolinones. In this reaction, DCM serves as a twofold electrophile, undergoing double C-Cl bond cleavage to react with hydrobenzoxazoles.
Article
Chemistry, Organic
Kai Yang, Pengfei Wang, Ze-Ying Sun, Minjie Guo, Wentao Zhao, Xiangyang Tang, Guangwei Wang
Summary: In this study, a hydrogen-bonding controlled nickel-catalyzed regioselective cyclotrimerization of terminal alkynes was reported, yielding 1,3,5-trisubstituted benzenes with high regioselectivities. The method features a low-cost catalyst, mild reaction conditions, and excellent functional group compatibility. The Ni-B(OH)(2) complex generated in situ from NiCl2·DME and tetrahydroxydiboron may act as an active catalyst for this transformation.
Article
Chemistry, Organic
Lingyun Yao, Yan Shang, Jian-Shu Wang, Ailin Pan, Jun Ying, Xiao-Feng Wu
Summary: This palladium-catalyzed carbonylative synthesis efficiently converts 2-alkynylanilines and aryl iodides into N-acyl indoles using TFBen as the CO source, resulting in high yields.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Dong Lu, Songhua Chen, Niu Tang, Shuang-Feng Yin, Nobuaki Kambe, Renhua Qiu
Summary: In this study, a method for producing 2-haloalkoxy-3-substituted quinolines via cyclization of 2-alkynylanilines with TMSCF3 and THF was described. This synthetic method utilizes inexpensive and easy-to-handle TMSCF3 and a commercially available CuI catalyst to efficiently transform a wide range of 2-alkynylanilines into versatile 2-difluoromethoxy-3-substituted quinolines and 2-iodoalkoxy-3-substituted quinolines with excellent chemoselectivity.
Article
Chemistry, Multidisciplinary
Binyang Jiang, Shi-Liang Shi
Summary: In this study, the first Pd-catalyzed aryl-alkyl cross-coupling of alkylzirconocenes and aryl halides was reported, with the critical role of a commercially available N-heterocyclic carbene (IPr) ligand for the palladium catalyst. This mild protocol tolerates various functional groups and heterocycles and is applicable to both terminal and internal alkenes.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Jing-Ao Ren, Jin-He Na, Chao Gui, Chengping Miao, Xue-Qiang Chu, Mengtao Ma, Hao Xu, Xiaocong Zhou, Zhi-Liang Shen
Summary: A nickel-catalyzed direct cross-coupling between unactivated aryl fluorides and aryl bromides was achieved. This one-pot reaction proceeds effectively at room temperature in THF, avoiding the use of preformed and sensitive organometallic reagents. The desired biaryls are produced in modest to good yields via C-F bond cleavage in the presence of a phosphine ligand and magnesium powder (with or without TMSCl).
Article
Chemistry, Organic
Yiming You, Jiawen Hu, Tao Wu
Summary: Few studies have been conducted on aryl-substituted allenyl monofluorides due to concerns about their stability. In this study, we report a copper-catalyzed regioselective synthesis of these structures using inexpensive and accessible aryl boronic esters under mild conditions. The arylated allenyl monofluorides were stable enough to be isolated and easily converted to various other fluorine-containing compounds. Preliminary asymmetric attempts indicated that the reaction could proceed via a selective beta-fluorine elimination process.
Article
Multidisciplinary Sciences
Dong Liu, Zhao-Ran Liu, Zhen-Hua Wang, Cong Ma, Simon Herbert, Hartmut Schirok, Tian-Sheng Mei
Summary: In this study, the authors investigated the electrochemical asymmetric catalysis by utilizing both the anode and cathode as working electrodes. The asymmetric cross-coupling between alpha-chloroesters and aryl bromides was successfully achieved, demonstrating the synergistic involvement of cathodic reduction and anodic oxidation in the paired electrolysis. This electrolytic method provides a promising alternative for asymmetric catalysis in organic synthesis.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Kaiting Zheng, Yaomei Liu, Chenggong Zheng, Fangpei Yan, Hua Xiao, Yi-Si Feng, Shilu Fan
Summary: A palladium-catalyzed monofluoroalkylation method using nucleophilic ethyl 2-fluoro-2-(trimethylsilyl)acetate as a monofluoroalkyl source was developed. The reaction exhibited excellent substrate scope, providing a range of monofluoroalkylated products in good yields under mild conditions. This protocol was successfully applied in the late-stage modification of an estrone derivative, offering a facile route for the discovery of biologically active compounds and high-performance materials.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Ruiting Yang, Qiumin Xie, Qian Yan, Xiuli Zhang, Bao Gao
Summary: A novel method for synthesizing thioesters using S-aryl thioformates as sources has been reported. The reaction achieved desirable yields of thioesters with various substrates under mild conditions. Gram-scale synthesis was also successful using this method.
