Article
Chemistry, Organic
Xiaoqin Ning, Yongke Chen, Fangdong Hu, Ying Xia
Summary: This study presents the palladium-catalyzed cross-coupling reactions of cyclobutanone-derived N-sulfonylhydrazones with aryl or benzyl halides, demonstrating that the metal carbene process and beta-hydride elimination can occur smoothly in strained ring systems to yield structurally diverse products. The preliminary success in asymmetric carbene coupling reactions in strained ring systems offers a promising route for the synthesis of enantioenriched four-membered-ring molecules.
Article
Chemistry, Multidisciplinary
Ji-Hang Xu, Zi-Kui Liu, Yan-Liu Tang, Yang Gao, Xiao-Qiang Hu
Summary: An unprecedented ring-opening cross-coupling of 1,2-oxazetidines with arylboronic acids using copper catalysis has been achieved. This reaction offers simple operation, inexpensive catalyst, broad scope, and high regioselectivity, leading to a wide range of aminomethylation products. Furthermore, the obtained products can be further transformed and bioactive acids can be modified.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Fang Wang, Qianting Zhou, Xinying Zhang, Xuesen Fan
Summary: A novel and efficient alpha-C(sp(3))-H alkenylation of cyclic amines with maleimides was presented, featuring readily available and structurally diverse substrates, a green and economical catalyst, a unique reaction pathway, mild reaction conditions, high efficiency, and excellent atom economy. This new reaction enriches the application of Fe(III)-catalyzed C(sp(3))-H activation and functionalization.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
C. M. A. Afsina, Thaipparambil Aneeja, Mohan Neetha, Gopinathan Anilkumar
Summary: Copper-catalyzed organic reactions have attracted widespread attention due to the abundance and affordability of copper, as well as its low toxicity, eco-friendliness, sustainable nature, and versatility as a catalyst. These reactions are primarily used for the synthesis of biologically important nitrogen heterocycles, amines, amides, imines, and alkynes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiang-Ting Min, Ding-Wei Ji, Yu-Qing Guan, Shi-Yu Guo, Yan-Cheng Hu, Boshun Wan, Qing-An Chen
Summary: Transition metal catalyzed decarbonylation offers a unique synthetic strategy for new chemical bond formation. The study developed a visible light induced rhodium catalysis for decarbonylative coupling of imides with alkynes under ambient conditions, revealing the rhodium complex serves as both the catalytic center and photosensitizer. This visible light promoted catalytic decarbonylation strategy opens up new opportunities for re-evaluating old transformations with ligand dissociation as a rate-determining step.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Lukas Hoff, Simon D. Schnell, Andrea Tomio, Anthony Linden, Karl Gademann
Summary: A silver-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids was presented in this study. It was found that electronic modification of the dppf ligand played a crucial role in achieving good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were successfully prepared, with yields up to 87%.
Article
Chemistry, Multidisciplinary
Johannes Grosskopf, Alexandra A. Heidecker, Thorsten Bach
Summary: Racemic 3-substituted oxindoles can be converted into enantiomerically pure or enriched material through photochemical deracemization process. Light energy compensates for the loss of entropy and enables predictable editing of the stereogenic center. The obtained oxindoles are valuable intermediates for further transformations with complete retention at the stereogenic center.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shahilan Ratnam, Shreya Unone, Daniel Janssen-Mueller
Summary: It is found that alkyl-substituted dihydroquinolines derived from 2,2'-biquinoline can serve as efficient radical precursors, forming primary, secondary, and tertiary alkyl radicals. Copper catalysis allows the hydroalkylation of benzalmalononitriles and N-Boc protected diazenes under mild conditions, with yields up to 85%. The reactivity of the dihydroquinolines towards denitrative alkylation of nitroolefins, such as β-nitrostyrene, has been discovered. Notably, the released biquinoline can be recycled, greatly improving the atom-economy of these alkyl radical precursors compared to previous N-heterocyclic electroauxiliaries.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Cong Zhang, Yuhang He, Guanghui An
Summary: Iron-mediated divergent reductive coupling reactions of heteroarenes with alkenes have been developed. By switching the substituent site at the C2 and C4 positions of quinolines, either C2 Minisci alkylation or C4 reductive alkylation could be achieved. These approaches feature mild conditions and sensitive functional group tolerance, which enables the functionalization of natural products and medicines. Mechanism investigation revealed that Fe(dibm)(3) would be a dual promoter for both alkyl radical transfer and generation of the more reactive hydrogen donor Ph(RO)SiH2.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Subrata Das, Andreas W. Ehlers, Sima Patra, Bas de Bruin, Buddhadeb Chattopadhyay
Summary: A concept for intermolecular C-N cross-coupling amination has been discovered using tetrazoles and aromatic and aliphatic azides with boronic acids under iron-catalyzed conditions. The reaction follows an unprecedented metalloradical activation mechanism, different from traditional metal-catalyzed C-N cross-coupling reactions. The wide scope of this reaction has been demonstrated by employing various tetrazoles, azides, and boronic acids. Moreover, the reaction has shown potential for applications in medicinal chemistry, drug discovery, and pharmaceutical industries, as demonstrated by late-stage aminations and synthesis of a drug candidate.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Xinyu Chen, Hongqiang Liu, Hui Gao, Pinhua Li, Tao Miao, Hongji Li
Summary: An electrochemical cross-dehydrogenative coupling of indoles with xanthenes has been achieved at room temperature without the need for any catalyst or external oxidant, yielding moderate amounts of indole derivatives. Mechanistic experiments suggest a possible involvement of a radical pathway in this reaction system.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Melanie Walther, Waldemar Kipke, Sven Schultzke, Souvik Ghosh, Anne Staubitz
Summary: Azobenzenes are widely used molecular switches that require further functionalization for specific tasks, which can be achieved through cross-coupling reactions. This review provides an overview of recent developments in modifying azobenzene and its derivatives using cross-coupling reactions.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Guo-Qiang Xu, Teng-Fei Xiao, Guo-Xuan Feng, Chen Liu, Baoxin Zhang, Peng-Fei Xu
Summary: The metal-free C(sp(3))-H aroylation of amines via visible-light photoredox catalysis provides a direct route for constructing a useful a-amino aryl ketone skeleton. Selected products show good biological activity for protecting PC12 cells, indicating the potential of this skeleton as a new neuroprotective agent. Mechanism experiments suggest that this transformation follows a photoredox catalytic radical-radical cross-coupling pathway.
Article
Chemistry, Multidisciplinary
Johannes Grosskopf, Manuel Plaza, Roger Jan Kutta, Patrick Nuernberger, Thorsten Bach
Summary: 2,5-Diketopiperazines are cyclic dipeptides with a wide range of applications, and their enantioselective preparation can be achieved through photochemical deracemization, allowing for stereochemical editing at a single position while maintaining other stereogenic centers unaffected. The chiral benzophenone catalyst in combination with irradiation at lambda=366 nm enables the establishment of configuration at the stereogenic carbon atom C6 at will.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Jianbin Li, Chia-Yu Huang, Chao-Jun Li
Summary: This review summarises recently developed strategies for achieving C-C cross-couplings between an inert aliphatic C-H bond and another C-H bond through different C(sp3)-H functionalisation tactics.
TRENDS IN CHEMISTRY
(2022)
Article
Chemistry, Organic
Miao Lai, Ke Zhai, Chuance Cheng, Zhiyong Wu, Mingqin Zhao
ORGANIC CHEMISTRY FRONTIERS
(2018)
Article
Chemistry, Organic
Zhiyong Wu, Miao Lai, Siyuan Zhang, Xianyun Zhong, Hao Song, Mingqin Zhao
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Chuance Cheng, Mingqin Zhao, Miao Lai, Ke Zhai, Bo Shi, Shuai Wang, Rui Luo, Linbao Zhang, Zhiyong Wu
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Miao Lai, Zhiyong Wu, Shi-Jun Li, Donghui Wei, Mingqin Zhao
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Miao Lai, Zhiyong Wu, Fangyao Su, Yujian Yu, Yanqiu Jing, Jinmin Kong, Zhenteng Wang, Shuai Wang, Mingqin Zhao
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Jingyan Hu, Xiefeng Ye, Shuai Hao, Qianrui Zhao, Mingqin Zhao, Yuewei Wei, Zhiyong Wu, Na Wang, Xiaoming Ji
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Zhiyong Wu, Shuai Hao, Jingyan Hu, Hongtao Shen, Miao Lai, Pengfei Liu, Gaolei Xi, Pengfei Wang, Shengchen Zhao, Xiaoping Zhang, Mingqin Zhao
Summary: This novel and facile synthesis of aryl benzyl sulfones was achieved for the first time through a copper-catalyzed decarboxylative reductive sulfonylation reaction between alpha-oxocarboxylic acids and aryl sulfonyl hydrazines. The protocol proceeds smoothly under simple conditions, offering advantages of simple operation, high yields, and good functional group compatibility. This approach introduces a conceptually novel methodology for aryl benzyl sulfone synthesis under a decarboxylative reductive progress.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Longfei Wang, SongShuang Ding, Hongtao Shen, Yiying Wang, Shuai Hao, Guangting Yin, Jianhua Qiu, Beisen Lin, Zhiyong Wu, Mingqin Zhao
Summary: This work demonstrates the amidation reactions of coumarin-3-carboxylic acids under mild conditions using tetraalkylthiuram disulfides as the amidation reagents. The protocol is compatible with a variety of functional groups and provides an attractive strategy for synthesizing coumarin-3-carboxamides in moderate to good yields.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Longfei Wang, Jianhua Qiu, Bohai Zhang, Mengqi Chen, Hongxia Wang, Xiaohui Miao, Zhiyong Wu, Mingqin Zhao, Hongtao Shen, Miao Lai, Xiangdong Shi
Summary: This article describes the nickel-catalyzed amidation of aryl alkynyl acids using tetraalkylthiuram disulfides as the amine source, resulting in the synthesis of a series of aryl alkynyl amides in good to excellent yields under mild conditions. This general methodology provides an operationally simple alternative pathway for the synthesis of useful aryl alkynyl amides, demonstrating its practical synthetic value in organic synthesis. The mechanism of this transformation was investigated through control experiments and DFT calculations.
Article
Chemistry, Multidisciplinary
Jingyan Hu, Xiaoming Ji, Shuai Hao, Mingqin Zhao, Miao Lai, Tianbao Ren, Gaolei Xi, Erbin Wang, Juanjuan Wang, Zhiyong Wu
