Article
Chemistry, Multidisciplinary
Elisa Y. Lai, Binbin Yuan, Lutz Ackermann, Magnus J. Johansson
Summary: In this study, a new method for directed ruthenium-catalyzed C-H aminocarbonylation has been developed under mild conditions through high-throughput experimentation. This method allows the introduction of special amide functional groups and is applicable to various substitution patterns and different weakly Lewis basic directing groups in anilides.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Wang Jiang, Xiuxiu Yang, Lin Lin, Chaoguo Yan, Yue Zhao, Minyan Wang, Zhuangzhi Shi
Summary: Metal-catalyzed C-H activation strategies provide an efficient approach for synthesis. In this study, visible-light-induced late-stage C-H activation was achieved using a single rhodium complex. The reaction offers advantages such as environmental friendliness and the utilization of inherent directing groups, providing a new platform for ligand design and preparation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Till Schmidt-Raentsch, Hendrik Verplancke, Jonas N. Lienert, Serhiy Demeshko, Matthias Otte, Gerard P. Van Trieste, Kaleb A. Reid, Joseph H. Reibenspies, David C. Powers, Max C. Holthausen, Sven Schneider
Summary: In this study, the synthesis of a formal terminal nitride complex of palladium was reported, and it was characterized through photocrystallography, magnetism, and computational methods. Based on this complex, a photocatalytic protocol for aldehyde C-H trimethylsilylamidation was developed, which exhibited inverted nucleophilic selectivity. This first example of catalytic C-H nitrogen atom transfer has significant implications for obtaining primary amides.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xu Yang, Meng-Xue Jiang, Tao Zhou, Ye-Qiang Han, Xue-Tao Xu, Kun Zhang, Bing-Feng Shi
Summary: This study presents a palladium-catalyzed asymmetric functionalization of unbiased methylene C(sp(3))-H bonds, using a specific directing group and chiral ligand to achieve high enantioselectivity in arylation reactions. The combination of aryl iodides with the chiral ligand was found to be beneficial for achieving high enantiocontrol. The PIP directing group could be easily removed without compromising enantiopurity.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Organic
Priyank Purohit
Summary: This article presents the challenge of regiospecific and atom economic C-C bond formation, which has been addressed by directing group and organometal-based C-H activation strategy. Organometals like Ru, Pd, Pt, Ni have been discovered as effective catalysts for C-H activation without the need for pre-activation of the inert C-H bond. This study focuses on cationic ruthenium and its unique reactivity with inert substrates.
CURRENT ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yangyang Wang, Xiaobo Xu, Binghan Pang, Liqiang Hao, Gaorong Wu, Yafei Ji
Summary: In this study, the palladium-catalyzed sequential C(sp(3))-H and C(sp(2))-H bond diolefination reaction of o-toluidine was achieved using acetyl-protected aminoethyl phenyl thioether ligands. This novel reaction allows for the preparation of conjugated diene structure via an immediate second olefination, based on the first C(sp(3))-H olefination, in one pot. Various triflyl-protected anilines and acrylates were elegantly used as coupling partners. Furthermore, the unpurified diolefination products can be easily converted to tetrahydroquinoline derivatives.
Article
Chemistry, Multidisciplinary
Md Emdadul Hoque, Ranjana Bisht, Anju Unnikrishnan, Sayan Dey, Mirja Md Mahamudul Hassan, Saikat Guria, Rama Nand Rai, Raghavan B. Sunoj, Buddhadeb Chattopadhyay
Summary: A method of para-selective borylation of aromatic amides is described using a newly designed ligand framework (defa), which shows excellent selectivity and reactivity for the para position. This method can contribute to the development of new catalytic systems and the synthesis of para-functionalized compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Applied
Mai Yanagawa, Shingo Harada, Shumpei Hirose, Tetsuhiro Nemoto
Summary: The study developed a rhodium-catalyzed C-H functionalization reaction for synthesizing 2,3-fused indole variants using an alpha,beta-unsaturated enone as a directing group and electrophile. This annulation enabled the rapid assembly of valuable hydrocarbazolones from readily available indoles, and computational investigations were conducted to elucidate the reaction pathway and site-selectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Lanxiao Zhao, Peng Deng, Xun Gong, Xiaohui Kang, Jianhua Cheng
Summary: This study demonstrated the catalytic ortho-regioselective C-H alkylation of alkoxy-substituted benzene derivatives with alkenes using a half-sandwich calcium alkyl complex as the precatalyst. The potential catalytic reaction intermediates were isolated and X-ray structurally characterized, with DFT calculations elucidating the different reaction profiles of sp(2) and sp(3) C-H activations.
Article
Chemistry, Applied
Xavier Marset, Marti Recort-Fornals, Malkaye Kpante, Adam Zielinski, Christopher Golz, Lawrence M. Wolf, Manuel Alcarazo
Summary: A series of strong it-acceptor polyfluorinated and dicationic chelating phosphines were synthesized and evaluated in the Rh-catalysed dimerization of norbornadiene, leading to the selective formation of specific products and site-selective arylation reactions. Theoretical calculations were performed to understand the origin of the observed regioselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Biochemistry & Molecular Biology
Ming Zeng, Jiaqi Chen, Fengye Li, Haojie Li, Lan Zhao, Dengzhao Jiang, Jun Dai, Wenbo Liu
Summary: 1,3,5-triazines, especially indole functionalized triazine derivatives, have shown excellent activities in anti-tumor, antibacterial, and anti-inflammatory fields. Traditional methods for synthesizing N-(2-triazine) indoles have limitations due to unstable materials and complex operations. In this study, an efficient ruthenium-catalyzed oxidative synthesis of N-(2-triazine) indoles by C-H activation was developed, resulting in moderate to good yields. The reaction proceeded through a proposed six-membered ruthenacycle intermediate, indicating the chelation assistance of the triazine ring in the formation of N-(2-triazine) indoles.
Article
Chemistry, Multidisciplinary
Yulei Wang, Hendrik Simon, Xinran Chen, Zhipeng Lin, Shan Chen, Lutz Ackermann
Summary: While electrochemical ortho-selective C-H activations are well established, the development of distal C-H activations is still limited. In this study, we report the electrochemical meta-C-H functionalization, achieving remote C-H bromination in an undivided cell under ligand- and electrolyte-free conditions. Notably, pyrazolylarenes were selectively brominated at the benzenoid moiety rather than the electron-rich pyrazole ring for the first time. Mechanistic studies suggested the formation of a ruthenacycle followed by a ligand-to-ligand hydrogen transfer (LLHT) process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Lin Lin, Xue-jun Zhang, Xinyu Xu, Yue Zhao, Zhuangzhi Shi
Summary: This study reports a modular assembly method for diverse phosphine-amide ligands, using ruthenium-catalyzed C-H activation of phosphines with isocyanate directed by phosphorus(III) atoms. The method enables efficient and selective synthesis of various phosphine-amide ligands, some of which show excellent efficiency for asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Xuefeng Tan, Xiaoyan Hou, Torben Rogge, Lutz Ackermann
Summary: This study achieved the electrochemical three-component assembly of isoquinolines using ruthenium electro-catalyzed C-H/N-H functionalization, demonstrating a robust electrocatalysis with ample substrate scope, efficient electrooxidation, and an operationally friendly procedure. Furthermore, detailed mechanistic studies and unprecedented cyclovoltammetric analysis of a seven-membered ruthenacycle supported an unusual ruthenium(II/III/I) regime.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Lukass Lukasevics, Aleksandrs Cizikovs, Liene Grigorjeva
Summary: An efficient protocol for the C(sp(2))-H carbonylation of amino acid derivatives based on an inexpensive cobalt(II) salt catalyst is reported. The method utilizes picolinamide as a traceless directing group and Co(dpm)(2) as the catalyst, allowing for a broad range of phenylalanine derivatives bearing diverse functional groups to be tolerated. Moreover, the method can be successfully applied for the C(sp(2))-H carbonylation of short peptides, enabling access for peptide late-stage carbonylation.
Article
Chemistry, Organic
Miki Murata, Yuna Maeda
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2019)
Article
Plant Sciences
Yoshihito Kohari, Shunsuke Yamashita, Tai-Ying Chiou, Yasutaka Shimotori, Naofumi Ohtsu, Yuichi Nagata, Miki Murata
JOURNAL OF ESSENTIAL OIL BEARING PLANTS
(2020)
Article
Biochemistry & Molecular Biology
Tai-Ying Chiou, Shiori Nomura, Masaaki Konishi, Chien-Sen Liao, Yasutaka Shimotori, Miki Murata, Naofumi Ohtsu, Yoshihito Kohari, Wei-Ju Lee, Tsung-Yu Tsai, Yuichi Nagata, Tohru Saitoh
Article
Chemistry, Organic
Kazumasa Kon, Hiromu Takai, Takumu Kobayashi, Yoshihito Kohari, Miki Murata
Summary: An organocatalyzed asymmetric aldol reaction of α-keto amides has been developed, with an N-terminal 4-trans-siloxyproline-based tripeptide as the catalyst, yielding aldol adducts with up to 99% yield and 91% ee.
Article
Polymer Science
Takeshi Namikoshi, Md. Saifur Rahman, Tamotsu Hashimoto
MACROMOLECULAR RESEARCH
(2021)
Article
Plant Sciences
Takahiro Ueda, Miki Murata, Ken Yokawa
Summary: This study found that different wavelengths of LED light can promote the biosynthesis of cyclic monoterpenes in mint leaves, with blue light supplementation showing the most significant effects.
Article
Polymer Science
Takeshi Namikoshi, Yuhei Watanabe, Ayaka Kaneda, Kazuma Ishikawa, Shinji Watanabe, Miki Murata
Summary: The living cationic polymerizations of sulfide-containing vinyl ethers were investigated, revealing that the nucleophilicity of the sulfur moiety influenced the polymerization process. Specifically, PSEVE polymerized smoothly while MSPEVE did not form cyclic sulfonium species during the reaction.
MACROMOLECULAR RESEARCH
(2022)
Article
Polymer Science
Guanwu Yin, Takeshi Namikoshi, Masahiro Teraguchi, Takashi Kaneko, Toshiki Aoki
Summary: In this study, five types of absolute asymmetric polymerizations were achieved, resulting in soluble high molecular weight chiral polymers without the use of chiral compounds or circularly polarized light. This new mechanism provides clues for a better understanding of the origin of chirality in our world.
Article
Polymer Science
Takeshi Namikoshi, Tamotsu Hashimoto, Naoto Shikano, Michio Urushisaki, Toshikazu Sakaguchi
Summary: This study synthesized a vinyl ether containing a cyclic carbonate group and formed hydroxyurethane polymers through reaction with alkanolamines. The results demonstrated that the hydroxyurethane polymers had different solubilities and thermal stabilities at different temperatures.
Article
Chemistry, Analytical
Naofumi Ohtsu, Masataka Gtoh, Kazuya Shirakawa, Tai-Ying Chiou, Yasutaka Shimotori, Yoshihito Kohari, Yuichi Nagata, Miki Murata
Summary: Hot-water treatment of Japanese peppermint powder can release polyphenol ingredients to enhance natural green food coloring. The treatment changes the color of the food product, while untreated powder results in a different color.
Article
Chemistry, Organic
Kazumasa Kon, Yoshihito Kohari, Miki Murata
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2020)
Article
Chemistry, Applied
Yasutaka Shimotori, Takumi Watanabe, Yoshihito Kohari, Tai-Ying Chiou, Naofumi Ohtsu, Yuichi Nagata, Miki Murata
JOURNAL OF OLEO SCIENCE
(2020)
Article
Food Science & Technology
Tai-Ying Chiou, Masaaki Konishi, Shiori Nomura, Yasutaka Shimotori, Miki Murata, Naofumi Ohtsu, Yoshihito Kohari, Yuichi Nagata, Tohru Saitoh
FOOD SCIENCE AND TECHNOLOGY RESEARCH
(2019)
Article
Food Science & Technology
Shiori Nomura, Wei-Ju Lee, Masaaki Konishi, Tohru Saitoh, Miki Murata, Naofumi Ohtsu, Yasutaka Shimotori, Yoshihito Kohari, Yuichi Nagata, Tai-Ying Chiou
FOOD SCIENCE AND TECHNOLOGY RESEARCH
(2019)
Article
Chemistry, Organic
Kazumasa Kong, Yoshihito Kohari, Miki Murata
