Article
Chemistry, Organic
Wen-Xin Li, Bo-Wen Yang, Xuan Ying, Zhuo-Wen Zhang, Xue-Qiang Chu, Xiaocong Zhou, Mengtao Ma, Zhi-Liang Shen
Summary: The direct cross-coupling of diaryl sulfoxides with aryl bromides via C-S bond cleavage was achieved using nickel(II) as the catalyst, 1,2-bis(diphenylphosphino)ethane (dppe) as the ligand, and magnesium turnings as the reducing metal in THF. This reaction showed a wide range of substrates and could be used for gram-scale synthesis. The one-pot reaction is operationally simple and economically efficient.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Chuntao Zhong, Mengna Liu, Xianchao Qiu, Hao Wei, Benqiang Cui, Yanhui Shi, Changsheng Cao
Summary: A nickel-catalyzed cross-coupling reaction between aryl methyl sulfides and aryl bromides has been developed to efficiently access biaryls. The method has a wide scope of substrates and is scalable, with commercially available aryl bromides being used without the need for preparation of organometallic reagents. This reaction has high application value.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Andrei A. . Leushukou, Anastasiya V. Krech, Alaksiej L. Hurski
Summary: In this study, a photocatalyst-free nickel-catalyzed cross-coupling reaction was reported, which achieved efficient alkylation of various organic halides using alkyltitanium alkoxides generated in situ from Grignard reagents and Ti(OiPr)(4) upon irradiation with blue light.
Article
Chemistry, Organic
Xinmiao Huang, Ling Tang, Zhiyong Song, Shuangshuang Jiang, Xianmao Liu, Ming Ma, Bo Chen, Yuanhong Ma
Summary: A nickel catalysis system has been developed for the desulfonylative C(sp(2))-C(sp(2)) reductive cross-coupling reactions of aryl sulfone derivatives with aryl bromides to form diverse biaryl compounds. The isolated and confirmed Ar-Ni(II)-SO(2)CF3 complex with a phosphine ligand through oxidative addition of aryl sulfone to Ni(0) species provides solid evidence for understanding the C(Ar)-SO2 bond activation and reaction mechanism.
Letter
Chemistry, Organic
Na-Na Ma, Xuan-Bo Hu, Yuan-Shuai Wu, Ya-Wen Zheng, Mengtao Ma, Xue-Qiang Chu, Hao Xu, Haiqing Luo, Zhi-Liang Shen
Summary: A direct cross-coupling reaction of aryl thioether with aryl bromide was successfully achieved using nickel salt, magnesium, and lithium chloride as catalysts in tetrahydrofuran solvent at room temperature. The one-pot reactions efficiently cleaved the C-S bond, yielding the desired biaryls in moderate to good yields, without the need for pregenerated or commercial organometallic reagents.
Article
Chemistry, Multidisciplinary
Lili Fang, Shuqi Jia, Shuaixin Fan, Jin Zhu
Summary: A palladium catalytic method has been developed for the coupling of amides and cyclopropanols to γ-diketones by simultaneously activating C-N and C-C bonds. Heteroatom ligand exchange and heteroatom-to-carbon ligation mode switching enable molecular cross-coupling in a context-dependent manner, without the need for stoichiometric organometallic reagents or bases.
CHEMICAL COMMUNICATIONS
(2023)
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, Organic
Chen Zhang, Na-Na Ma, Zi-Lun Yu, Chuanji Shen, Xiaocong Zhou, Xue-Qiang Chu, Weidong Rao, Zhi-Liang Shen
Summary: The efficient palladium-catalyzed direct reductive cross-coupling reaction proceeds smoothly at room temperature with moderate to good yields, showing reasonable functional group tolerance. The one-pot reaction using readily available aryl bromide as a coupling partner is simple to handle, avoiding the use of pre-prepared organometallic reagents.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Na-Na Ma, Jing-Ao Ren, Xiang Liu, Xue-Qiang Chu, Weidong Rao, Zhi-Liang Shen
Summary: The direct cross-couplings of aryl sulfonium salts with aryl halides using nickel as a reaction catalyst were successfully achieved. The reactions proceeded efficiently via C-S bond activation at ambient temperature, providing moderate to good yields, potentially serving as an attractive alternative to conventional cross-coupling reactions.
Article
Chemistry, Organic
Yunxia Liu, Xin Li, Qing Liu, Xinjin Li, Hui Liu
Summary: The electromagnetic mill (EMM) has enabled the palladium-catalyzed borylation of aryl bromides under solvent-free conditions with low palladium catalyst loading (0.05-0.5 mol %). This method offers numerous advantages, including a wide substrate scope, tolerance towards various functional groups, short reaction times, no additional heating requirements, and practical gram-scale synthesis. The EMM system not only shows promising potential for industrial applications, but also expands the possibilities of solvent-free solid-state metal-catalyzed syntheses.
Article
Chemistry, Physical
Dong-Song Zheng, Wen-Wen Zhang, Qing Gu, Shu-Li You
Summary: The rhodium-catalyzed enantioselective C-H iodination of 1-aryl isoquinolines with N-iodosuccinimide (NIS) is presented, affording axially chiral biaryl iodides in excellent yields and enantioselectivity. The reaction is also compatible with C-H bromination and chlorination, and the resulting biaryl iodides can be easily transformed to QUINAP-type and N,N-type chiral ligands.
Article
Chemistry, Inorganic & Nuclear
Gilian T. Thomas, Kiera Ronda, J. Scott McIndoe
Summary: The cross-coupling of N-tosylhydrazones and aryl halides to form carbon-carbon bonds, producing 1,1-disubstituted alkenes, has been widely used in chemistry, but its mechanism remains experimentally unexplored. The combination of benchtop NMR and real-time mass spectrometry allows for monitoring of catalytic intermediates and the rate of product formation.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Organic
Xiaolan Li, Haiqing Luo, Ruixin Song, Yuting Zhang, Xian Gong, Hu Cai, Xuzhong Luo
Summary: The developed methodology demonstrates an efficient Rh(III)-catalyzed oxidative C-H/C-H cross-coupling reaction between acyclic enamides and heteroarenes. This reaction offers advantages of excellent regio- and stereoselectivity, good compatibility with various functional groups, and a broad range of substrates. Mechanistically, Rh(III)-catalyzed β-C(sp(2))-H activation of acyclic enamides is proposed as the crucial step.
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, Applied
Masami Kuriyama, Genki Maeda, Kazuya Kamata, Yusuke Kodama, Kosuke Yamamoto, Osamu Onomura
Summary: The nickel-catalyzed cross-coupling of bromodifluoromethylphosphonates with arylboron reagents was achieved using a 1,10-phenanthroline-type ligand. Functionalized and heterocycle-containing boroxines were suitable partners for this reaction, and the catalytic modification of biologically active molecules, such as fenofibrate and indomethacin, was successfully accomplished. Moreover, the gram-scale reaction proceeded smoothly with a high yield of desired product.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
