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Chemistry, Multidisciplinary
Cristian Cavedon, Sebastian Gisbertz, Susanne Reischauer, Sarah Vogl, Eric Sperlich, John H. Burke, Rachel F. Wallick, Stefanie Schrottke, Wei-Hsin Hsu, Lucia Anghileri, Yannik Pfeifer, Noah Richter, Christian Teutloff, Henrike Mueller-Werkmeister, Dario Cambie, Peter H. Seeberger, Josh Vura-Weis, Renske M. van der Veen, Arne Thomas, Bartholomaus Pieber
Summary: We demonstrate visible-light-mediated carbon-heteroatom cross-coupling reactions using a photoactive Ni(II) precatalyst. The activation of this precatalyst involves an initial intraligand charge transfer event triggered by visible light irradiation. Additionally, a porous, recyclable organic polymer for heterogeneous nickel catalysis of cross-coupling reactions is obtained through ligand polymerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Remi Lavernhe, Ruben O. Torres-Ochoa, Qian Wang, Jieping Zhu
Summary: A versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes has been developed, leading to the synthesis of medicinally important heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Bijan Mirabi, Austin D. Marchese, Mark Lautens
Summary: In this study, a nickel-catalyzed cross-electrophile coupling reaction of aryl chlorides and heteroaryl chlorides was reported, enabled by a synergistic combination of halide effects and the addition of a magnesium salt. Electronic-deficient aryl chlorides were found to perform the best in the reaction, and preliminary mechanistic evidence showed that MgCl2 is crucial for accelerating the reduction of Ni(II) while small quantities of iodide lead to improved yields.
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, Physical
Xin-Shen Liang, Rui-Dong Li, Wei Sun, Zhong Liu, Xiao-Chen Wang
Summary: Borane-mediated hydride abstraction has been shown to be a powerful tool for the C(sp(3))-H functionalization of amines, but its activity with ethers is still unknown. In this study, we discovered this activity in 2H-chromenes and established a catalytic C(sp(3))-H functionalization reaction using silyl ketene acetals as nucleophiles.
Article
Chemistry, Multidisciplinary
Nikki J. Bakas, Jeffrey D. Sears, William W. Brennessel, Michael L. Neidig
Summary: This study provides critical insights into the role of TMEDA as an additive in iron-catalyzed cross-coupling reactions. By using spectroscopic and crystallographic techniques, TMEDA-iron(II)-aryl intermediates are identified in the reaction cycle and it is found that their recombination with radicals leads to highly selective product formation. This research highlights the significance of TMEDA in modulating the selectivity and catalytic performance of organoiron species in cross-coupling reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Manoj V. Mane, Sayan Dutta, Luigi Cavallo, Bholanath Maity
Summary: In recent years, there has been a growing interest in multicomponent reactions (MCRs) as environmentally friendly and reliable synthetic strategies for drug discovery. This article discusses theoretical investigations that unravel the mechanistic pathways in IrIII-CuII dual-catalyzed MCRs, experimentally reported by MacMillan, and explains the origin of selectivity between three-component and two-component coupling products. The results suggest that N-H bond activation is the rate-limiting step and the preference for a two-component product is governed by the relative stabilities of the CuII-X center dot intermediates.
Article
Chemistry, Multidisciplinary
Kouki Matsubara
Summary: The development of new N-heterocyclic carbene (NHC)-Ni complexes as catalysts has shown promising results, including the discovery of NHC-Ni(I) intermediates with excellent catalytic activity. Different types of Ni(I) complexes, such as dinuclear and mononuclear, have been identified as intermediates in these catalytic reactions, leading to a better understanding of the reaction mechanisms and potential prospects.
Article
Chemistry, Physical
Dominik Birnthaler, Rok Narobe, Eliseo Lopez-Berguno, Christoph Haag, Burkhard Koenig
Summary: Ligand-to-metal charge transfer (LMCT) photo-catalysis enables the activation and utilization of halides and other heteroatoms in metal complexes. The application of bismuth LMCT in organic radical coupling reactions has been expanded, generating chlorine and carboxyl radicals in net-oxidative and redox-neutral photochemical reactions. The study reveals BiCl4- and BiCl52- as the catalytically active bismuth species under 385 nm irradiation, providing insight into the reactivity of the highly reactive bismuth(II) catalyst fragment through cyclic voltammetry and UV-vis studies.
Article
Chemistry, Applied
Miguel A. Munoz-Torres, Fernando Martinez-Lara, Marta Solas, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The combination of organolithium chemistry with gold catalysis offers a new synthetic strategy for accessing polysubstituted indoles and carbazoles. This method utilizes ketopyrroles as starting materials and involves a series of reactions to selectively synthesize the desired products.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Zhenghong Zhou, Jimin Yang, Bo Yang, Yang Han, Lijuan Zhu, Xiao-Song Xue, Feng Zhu
Summary: This study presents a pioneering example of nickel-catalysed enantioconvergent Stille cross-coupling reactions. The reactions result in the formation of C-C bonds in good to high yields with excellent stereoselectivity, providing a practical and cost-effective method for synthesis. The innovative use of synergistic photoredox/nickel catalysis enables a novel single-electron transmetalation process, opening up new research possibilities in the field of Stille reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Fernando Martinez-Lara, Anisley Suarez, Noelia Velasco, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The gold-catalyzed transformation of propargylic glycols with thiols results in the formation of alpha-indol-3-yl alpha-((Z)-2-thioalkenyl) ketones through a complex but selective reaction mechanism. This sequence involves regioselective thiolation of indolyl diols followed by the attack of sulfur on the activated alkyne, rather than the indole. The final compounds are obtained in high yields from simple starting materials such as indolyl acyloins, ethynyl magnesium bromide, and thiols.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Lilian Geniller, Marc Taillefer, Florian Jaroschik, Alexis Prieto
Summary: The Ni-photoredox catalyzed desulfurative cross-coupling reaction enables the synthesis of various unsymmetrical diarylmethane molecules under mild reaction conditions, providing new transformations of abundant, naturally occurring thiols.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Multidisciplinary
Luiz S. Longo, Fernanda A. Siqueira, Nicolas S. Anjos, Gabriela F. D. Santos
Summary: This review summarizes the recent progress on the use of scandium(III) triflate as a Lewis acid catalyst for multicomponent reactions in the synthesis of nitrogen-containing heterocycles, which are valuable privileged scaffolds in Organic and Medicinal Chemistry.
Review
Chemistry, Organic
Natalie Hofmann, Kai C. Hultzsch
Summary: ADC and HT are powerful tools in the multicomponent formation of N-heterocycles, starting from simple and commercially available reagents. Base metal-catalyzed strategies, using manganese, iron, cobalt, nickel, and copper catalysts, have become increasingly important in recent years. These strategies are highly atom-efficient and environmentally friendly, with no need for further reducing or oxidizing agents.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Naifu Hu, Guoqing Zhao, Yuanyuan Zhang, Xiangqian Liu, Guangyu Li, Wenjun Tang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
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Chemistry, Multidisciplinary
Xiangqian Liu, Chien-Chi Hsiao, Indrek Kalvet, Matthias Leiendecker, Lin Guo, Franziska Schoenebeck, Magnus Rueping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Multidisciplinary
Lin Guo, Xiangqian Liu, Christoph Baumann, Magnus Rueping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Physical
Lin Guo, Chien-Chi Hsiao, Huifeng Yue, Xiangqian Liu, Magnus Rueping
Article
Chemistry, Organic
Huifeng Yue, Lin Guo, Xiangqian Liu, Magnus Rueping
Article
Chemistry, Physical
Xiangqian Liu, Jiaqi Jia, Magnus Rueping
Article
Chemistry, Organic
Xiangqian Liu, Chien-Chi Hsiao, Lin Guo, Magnus Rueping
Article
Chemistry, Multidisciplinary
Guodu Liu, Xiangqian Liu, Zhihua Cai, Guangjun Jiao, Guangqing Xu, Wenjun Tang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2013)
Article
Chemistry, Multidisciplinary
Teerawut Bootwicha, Xiangqian Liu, Roman Pluta, Iuliana Atodiresei, Magnus Rueping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2013)
Article
Chemistry, Multidisciplinary
Magnus Rueping, Xiangqian Liu, Teerawut Bootwicha, Roman Pluta, Carina Merkens
CHEMICAL COMMUNICATIONS
(2014)
Article
Chemistry, Organic
Xiangqian Liu, Hui Zhang, Yongwen Jiang
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Organic
Liu Shi, Xiangqian Liu, Hui Zhang, Yongwen Jiang, Dawei Ma
JOURNAL OF ORGANIC CHEMISTRY
(2011)
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Chemistry, Multidisciplinary
Xiangqian Liu, Huifeng Yue, Jiaqi Jia, Lin Guo, Magnus Rueping
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
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Chemistry, Multidisciplinary
Huifeng Yue, Lin Guo, Shao-Chi Lee, Xiangqian Liu, Magnus Rueping
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
