Article
Polymer Science
Naoki Shida, Kazuyuki Ninomiya, Natsuki Takigawa, Keiichi Imato, Yousuke Ooyama, Ikuyoshi Tomita, Shinsuke Inagi
Summary: A postpolymerization nucleophilic aromatic substitution reaction is used to efficiently diversify conjugated polymers, with complete substitution achieved by thiophenol derivatives and carbazole, while disubstitution occurs with para-selectivity by phenol derivatives.
Correction
Chemistry, Multidisciplinary
Kun-Xu Teng, Li-Ya Niu, Yan-Fei Kang, Qing-Zheng Yang
Summary: This study discusses a rational design of a dual lock-and-key supramolecular photosensitizer based on aromatic nucleophilic substitution for specific and enhanced photodynamic therapy.
Article
Chemistry, Multidisciplinary
Eduardo Rodrigo, Rainer Wiechert, Magnus W. Walter, Wilfried Braje, Herve Geneste
Summary: By using KOH, the direct F to OH exchange of aromatic and heteroaromatic substrates can be achieved under mechanochemical conditions, making the process more atom economical and environmentally friendly compared to other methods.
Article
Chemistry, Multidisciplinary
Mariel M. Cardenas, Mirza A. Saputra, Deane A. Gordon, Andrea N. Sanchez, Nobuyuki Yamamoto, Jeffrey L. Gustafson
Summary: In this study, we reported the catalytic atroposelective syntheses of pharmaceutically relevant 3-arylquinolines through SNAr reactions mediated by Cinchona alkaloid-derived ureas. These reactions exhibited a range of dynamic kinetic resolution (DKR) and kinetic resolution (KR) characteristics, with different pathways depending on the stereochemical stability of the starting material. Furthermore, functionalization of the atropisomerically enriched quinolines into pharmaceutically privileged scaffolds was achieved with minimal observed racemization.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Organic
Harry C. Sample, Mathias O. Senge
Summary: The study details the SNAr reactions of seven types of porphyrinoids with different pyrrole units, analyzing the substitution dependent on the type of nucleophile and the site of substitution. Nucleophilic substitution on porphyrinoids is found to be an cost-effective procedure with the ability to yield complex substituent patterns, regardless of the type of porphyrinoid.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Ritesh Gautam, Ian Geniza, Scott T. Iacono, Chadron M. Friesen, Abby R. Jennings
Summary: Perfluoropyridine (PFPy) is a highly reactive organofluorine compound that has versatile applications, including chemical synthesis, fluoropolymers, and fluorinated network materials.
Article
Chemistry, Multidisciplinary
Jie Zhang, Zuowei Xie
Summary: This study reported a pyridine-enabled transition-metal-free regioselective nucleophilic aromatic cage B(4)-H amination reaction, offering a selective amination strategy for o- and m-carboranes. Control experiments indicated the crucial role of magnesium complex, bidentate ligand, and reaction temperature in the process of cage isomerization.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Junu Kim, Yusuke Hayashi, Sara Badr, Kazuya Okamoto, Toshikazu Hakogi, Haruo Furukawa, Satoshi Yoshikawa, Hayao Nakanishi, Hirokazu Sugiyama
Summary: Extensive kinetic studies were conducted to identify new reaction pathways and evaluate their feasibility in resolving contradictions in the understanding of amination reaction via nucleophilic aromatic substitution. The use of different bases in the reaction system resulted in distinct concentration profiles, including sigmoidal profiles in both starting material and product. These profiles suggests that a species acting as a catalyst evolves during the reaction, indicating that the reaction mechanism changes depending on the specific base. The study presents novel identification of reaction conditions and additives that induce mechanism changes, while elucidating the catalytic effect of a newly discovered species formed during the reaction, thereby resolving the previously conflicting explanations of the reaction pathways.
REACTION CHEMISTRY & ENGINEERING
(2023)
Article
Chemistry, Multidisciplinary
Guangyu Zhang, Jiaxi Xu
Summary: In this study, a new cascade reaction involving the nucleophilic substitution, O[1,3] sigmatropic shift, Smiles rearrangement, and amide and ester exchange reaction was observed. It resulted in the synthesis of 2-((2/4-nitroaryl)amino)aryl carboxylate derivatives from 2/4-nitroaryl halides and N-acyl-N-arylhydroxylamines in the presence of sodium hydride in THF. This reaction provides a novel strategy for the synthesis of 2-hydroxydiarylamine derivatives under transition metal-free conditions.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Alexei Lukin, Mikhail Chudinov, Tatiana Vedekhina, Elizaveta Rogacheva, Lyudmila Kraeva, Olga Bakulina, Mikhail Krasavin
Summary: This study reported a new derivative of ciprofloxacin and synthesized 36 new fluoroquinolone derivatives through the synthesis of previously reported and newly synthesized derivatives of 1-oxa-9-azaspiro[5.5]undecane. The antibacterial experiments showed that compared to ciprofloxacin, the new compounds had a narrower activity spectrum, but displayed significant activity against two strains: Acinetobacter baumannii 987 (R) and Bacillus cereus 138 (R).
Article
Biochemistry & Molecular Biology
Kotaro Kikushima, Haruka Koyama, Kazuki Kodama, Toshifumi Dohi
Summary: The study demonstrates metal-free synthesis of monosubstituted aromatic compounds via nucleophilic aromatic substitution reactions, resulting in functionalized PTH derivatives through two-step reactions, some of which show potential application as photocatalysts for carbon-halogen bond reduction.
Article
Biochemistry & Molecular Biology
Taku Shoji, Mutsumi Takeuchi, Mayumi Uda, Yukino Ariga, Akari Yamazaki, Ryuta Sekiguchi, Shunji Ito
Summary: In this paper, a procedure for the synthesis of azuleno[2,1-b]quinolones and quinolines from 2-arylaminoazulene derivatives is described. The synthesis of azuleno[2,1-b]quinolones was achieved by the Bronsted acid-catalyzed intramolecular cyclization of 2-arylaminoazulene derivatives. The halogenative aromatization of azuleno[2,1-b]quinolones yielded azuleno[2,1-b]quinolines with a chlorine substituent at the pyridine moiety. The aromatic nucleophilic substitution reaction of these quinolines with secondary amines produced the corresponding aminoquinoline derivatives.
Article
Chemistry, Physical
Anthony R. Allen, Jia-Fei Poon, Rory C. McAtee, Nicholas B. Watson, Derek A. Pratt, Corey R. J. Stephenson
Summary: Alkene aminoarylation with arylsulfonylacetamides via visible light-mediated radical Smiles-Truce rearrangement is a convenient method for synthesizing the traditional arylethylamine pharmacophore generated by multistep reactions. Our detailed study on the mechanism suggests that the reaction may proceed through a stepwise process or concerted fashion.
Article
Chemistry, Multidisciplinary
Lucie Finck, Martin Oestreich
Summary: This study presents a chemoselective C(sp(2))-C(sp(2)) coupling of electron-deficient fluorinated arenes and functionalized N-aryl-N'-silyldiazenes as masked aryl nucleophiles. The fluoride-promoted transformation involves in situ generation of aryl nucleophiles with sensitive functional groups followed by a stepwise SNAr reaction. These reactions proceed rapidly at room temperature, allowing for functionalization of both coupling partners and yielding highly fluorinated biaryls in good yields.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Panagiota Kafourou, Byoungwook Park, Joel Luke, Luxi Tan, Julianna Panidi, Florian Glocklhofer, Jehan Kim, Thomas D. Anthopoulos, Ji-Seon Kim, Kwanghee Lee, Sooncheol Kwon, Martin Heeney
Summary: This report introduces a new high electron affinity acceptor end group TCNBT for use in n-type organic semiconductors, demonstrating improved molecular properties and orientation. Organic field-effect transistors based on TCNBT showed a high charge-carrier mobility and excellent ambient stability, highlighting the benefits of the cyanated end group and synthetic approach.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)