Article
Chemistry, Multidisciplinary
Ling Yang, Dong-Hang Tan, Wen-Xin Fan, Xu-Ge Liu, Jia-Qiang Wu, Zhi-Shu Huang, Qingjiang Li, Honggen Wang
Summary: A new method was proposed utilizing benzyl N-methyliminodiacetyl (MIDA) boronates for photochemical radical C-H halogenation, enabling successful fluorination, chlorination, and bromination reactions. The resulting brominated product could be further transformed into a variety of organic compounds, including those difficult to form with alpha-halo sp(2)-B boronate esters, by reaction with different nucleophiles. An activation effect of the B(MIDA) moiety was discovered.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xinyao Li, Johannes Grosskopf, Christian Jandl, Thorsten Bach
Summary: 3-Substituted quinoxalin-2(1H)-ones and various aryl-substituted or tethered olefins can undergo an enantioselective aza Paterno-Buchi reaction upon irradiation with a chiral sensitizer at lambda=420 nm. The absolute and relative configuration of the products were elucidated by X-ray crystallography, suggesting triplet energy transfer in a hydrogen-bonded complex between the imine substrate and the catalyst. Preliminary experiments also explored intramolecular cycloaddition and alternative reaction modes of quinoxalinones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Johanna Proessdorf, Christian Jandl, Thomas Pickl, Thorsten Bach
Summary: It was found that while 2-alk-omega-enyloxy-sustituted benzaldehydes do not display any photochemical reactivity at the arene core, the respective iminium perchlorates undergo efficient reactions under certain conditions, leading to products with different molecular structures and stereochemical features.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Robert D. Riley, Blake S. N. Huchenski, Karlee L. Bamford, Alexander W. H. Speed
Summary: This study demonstrates that diazaphospholene hydrides can be regenerated by the combination of phenylsilane and alkali metal salts, enabling catalytic radical reactions of aryl iodides. The method is not only applicable to aryl iodides, but can also be extended to aryl bromides, which benefit from visible light irradiation. Additionally, intermolecular radical hydroarylation reactions with arenes, thiophenes, and a pyridine have been successfully achieved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Kun-Quan Chen, He Sheng, Qiang Liu, Pan-Lin Shao, Xiang-Yu Chen
Summary: In recent years, NHC-catalyzed radical reactions have been gaining attention for their potential to create new activation modes previously inaccessible. Further research and understanding of this emerging area is warranted to explore its synthetic techniques and advantages.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Philipp Lenz, Ryo Oshimizu, Sina Klabunde, Constantin G. Daniliuc, Christian Mueck-Lichtenfeld, Jonas C. Tendyck, Tatsuya Mori, Werner Uhl, Michael Ryan Hansen, Hellmut Eckert, Shigehiro Yamaguchi, Armido Studer
Summary: This article presents a new type of oxy-borylenes as photoreductants. Experimental results demonstrate that these oxy-borylenes can exhibit strong reducing capability under visible light, making them suitable for various reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Tian Ye, Jinjin Zhao, Wan-Xin Zheng, Junmin Zhang, Zhijuan Wang, Feng-Lian Zhang
Summary: A silyl radical-triggered radical addition-translocation-cyclization (RATC) process has been developed to synthesize structurally diverse silicon-incorporated indolines. The reaction involves silyl radical addition, 1,5-hydrogen atom transfer (HAT), and cyclization, leading to the formation of indoline framework. The substituents attached to the radical center can influence the subsequent reactions, including exclusive hydrogen atom transfer, radical 1,4-silyl migration, and oxidation/deprotonation process. These chemo-divergent reactions provide easy access to silicon-modified indolines from simple starting materials.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Jie Liu, Gregor S. Cremosnik, Felix Otte, Axel Pahl, Sonja Sievers, Carsten Strohmann, Herbert Waldmann
Summary: This study presents the design and synthesis of a collection of 155 pyrroquinoline pseudo-NPs, combining fragments characteristic of tetrahydroquinoline and pyrrolidine classes in novel arrangements. Cheminformatic analysis and biological evaluation revealed chemically diverse pseudo-NP classes with distinct bioactivity patterns, dependent on fragment connectivity and regioisomeric arrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Nora Debreczeni, Miklos Bege, Aniko Borbas
Summary: In this study, we developed S-linked sugar-nucleotide analogues through radical mediated hydrothiolation, and constructed morpholino type mimetics using thio-click reactions and photoinitiated additions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Applied
Ramen Jamatia, Avijit Mondal, Dipankar Srimani
Summary: Manganese as a novel visible-light-induced catalyst shows great promise in terms of economic sustainability and applicability, leading to significant advancements in organic, polymer, and materials chemistry fields in recent years. Through manganese-catalyzed reactions, late-stage functionalization of valuable compounds and natural products can be realized, which is important for the development of medicinal and pharmaceutical chemistry.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Sota Adachi, Genki Horiguchi, Hidehiro Kamiya, Yohei Okada
Summary: Radical cation cycloadditions are intensively studied chemical transformations in modern synthetic organic chemistry. By generating and controlling highly reactive radical cation intermediates, various four- and six-membered ring compounds can be constructed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Karine Porte, Margaux Riomet, Carlotta Figliola, Davide Audisio, Frederic Taran
Summary: Click chemistry and bio-orthogonal reactions are primarily based on cycloaddition reactions, especially 1,3-dipolar cycloadditions. Mesoionic compounds have recently emerged as attractive dipole partners due to their ability to be derivatized and have their reactivity tuned towards cycloaddition reactions. Some compounds from the mesoionic family can also undergo click-and-release reactions, showing interesting applications in cells and animals.
Article
Chemistry, Organic
Aurelien Galibert-Guijarro, Dominique Mouysset, Liliane Mimoun, Michele P. Bertrand, Laurence Feray
Summary: The one-pot synthesis of 2-aminofurans was achieved through the Mn(OAc)3/Cu(OAc)2-mediated reaction between yna-mides derived from oxazolidone or 3-methylindole carboxylate and cyclic alpha-dicarbonyl radicals. This transformation involves several steps including addition, oxidation, and cyclization, resulting in the formation of persubstituted 2-aminofurans in high yields. This study presents the first radical route for the synthesis of furans from ynamides.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yusuke Imamura, Kyohei Takaoka, Yuma Komori, Masanori Nagatomo, Masayuki Inoue
Summary: This study presents a 34-step synthesis of Taxol, involving inter- and intramolecular radical reactions to connect the A- and C-ring fragments and cyclize the B-ring. The A- and C-ring functional groups were then efficiently modified using newly developed selective reactions. The construction of the D-ring and its conjugation with the beta-amino acid led to the successful synthesis of Taxol. This synthesis provides useful insights for the design of multistep syntheses of diverse bioactive natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Jose Laxio Arenas, Benoit Crousse
Summary: 1,2,3-triazoles are important scaffolds, with 4- and 5-halo triazoles playing a key role in their synthesis and providing a platform for chemical diversity around the 4 and 5 positions. The synthesis of 5- and 4-fluoro 1,2,3-triazoles remains challenging and will be presented separately due to their relative difficulty.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)