Article
Chemistry, Organic
Giampiero Proietti, Julius Kuzmin, Azamat Z. Temerdashev, Peter Diner
Summary: Perfluorinated aromatic nitrenes can react with sulfinamides and sulfoxides to generate achiral and chiral SIAs and SOIs, with one enantiopure SIA serving as a novel chiral auxiliary in Grignard additions to imines, yielding the product in up to 96:4 diastereomeric ratio.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Luis I. Domenianni, Markus Bauer, Till Schmidt-Raentsch, Joerg Lindner, Sven Schneider, Peter Voehringer
Summary: Transition-metal nitrides/nitrenes are promising reagents for catalytic nitrogen-atom-transfer reactions. They are prepared in situ via optically induced N-2 elimination from azido precursors. This study elucidates the primary molecular-level mechanisms responsible for the formation of a unique platinum(II) nitrene with a triplet ground state from a closed-shell platinum(II) azide precursor.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Hai -Bing Ye, Xu-Yu Zhou, Lei Li, Xiang-Kui He, Jun Xuan
Summary: Here we present a simple photochemical method for constructing phenanthridines with synthetically useful succinate units. The reaction proceeds under visible-light irradiation using cheap eosin Y Na as the photoredox catalyst and a diazo compound as the succinate precursor. A wide range of phenanthridines are obtained in moderate to good yields under the optimal conditions. The succinate units in the final heterocycles can be easily transformed into valuable structures such as gamma-butyrolactone, dihydrofuran-2(3H)-one, and tetrahydrofuran. Mechanistic experiments support the proposed mechanism.
Article
Chemistry, Organic
Chuan Wan, Yuan Feng, Zhanfeng Hou, Chenshan Lian, Liang Zhang, Yuhao An, Jinming Sun, Dongyan Yang, Chenran Jiang, Feng Yin, Rui Wang, Zigang Li
Summary: A novel amidation strategy using electrophilic sulfonium has been developed, enabling efficient amidation reactions in aqueous environments and solid-phase peptide synthesis. It also finds applications in peptide/protein modifications and activity-based protein profiling of a proteome at pH 10. Additionally, this method was used for peptide ligand-directed labeling of the USP7-UBL2 domain.
Article
Chemistry, Organic
Thomas Abegg, Janine Cossy, Christophe Meyer
Summary: cis-1,2-Dialkenylcyclopropanes with a vinyl azide group were generated by Knoevenagel condensations and underwent cascade Cope and Winstein [3,3]-sigmatropic rearrangements under mild conditions. This reaction sequence allows for the synthesis of diversely substituted 1,4-cycloheptadienes with a secondary allylic azide containing up to three stereocenters.
Article
Biochemistry & Molecular Biology
Vera A. Vil, Sergei S. Grishin, Alexander O. Terent'ev
Summary: An electrochemical method for synthesizing imidazoles has been developed, resulting in a wide range of products with high yields. The process involves multiple steps, including the generation of electrophilic iodine species, the formation of 2H-azirine from vinyl azide, and the reactions with benzyl amine and imine generated from benzyl amine. Despite the potential reduction of unsaturated intermediates with C=N bonds, the synthesis of imidazoles proceeds efficiently.
Article
Chemistry, Multidisciplinary
Kunlayanee Punjajom, Paul P. Sinclair, Ishika Saha, Mark Seierstad, Michael K. Ameriks, Pablo Garcia-Reynaga, Terry P. Lebold, Richmond Sarpong
Summary: A modular approach to dihydro-1,2,5-thiodiazole dioxide heterocycles is reported. Mechanistic and computational studies support an unusual 1,2 nitrogen migration mechanism for this transformation.
Article
Chemistry, Organic
Li-Jia Chen, Chia-Jou Kuo, Chien-Fu Liang
Summary: In this study, an efficient method for synthesizing aryl amides from sodium thiosulfate pentahydrate, organic anhydrides, and aryl azides was developed. Sodium thiosulfate acted as the sulfur source, reacting with anhydrides to generate acyl-Bunte salt which then reacted with aryl azides. The method successfully produced a key bioactive compound. The advantages of this one-pot two-step reaction include simplicity, diverse products with high yields, use of non-toxic reagents, and applicability to large-scale operations.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Guilherme L. Kosteczka, Rafael N. Soek, Wagner E. Richter, Renan B. Campos
Summary: This study explores the competitive formation of isomeric bridged lactams via acid-catalyzed intramolecular Schmidt reactions from 3-azidoethylcyclopentanones using density functional theory (DFT) calculations. The results indicate that specific substituents at alpha-carbons can efficiently control the reaction's regioselectivity through lone pair-cation interactions or steric hindrance, while cation-pi interactions are less effective.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
Yujing Guo, Chao Pei, Rene M. Koenigs
Summary: This study demonstrates the application of iminoiodinanes in amination reactions under visible light photochemical conditions. The authors investigate the formation and reactivity of triplet nitrenes and nitrene radical anions, compare both reagents, and showcase their applications in organic synthesis.
NATURE COMMUNICATIONS
(2022)
Article
Agriculture, Multidisciplinary
Takeshi Adachi, Yusuke Suzuki, Takuo Fujisawa
Summary: The photodegradation behavior of a new anilide fungicide inpyrfluxam was studied in aqueous buffer and nitrate solutions under artificial sunlight irradiation. The degradation mainly occurred via oxidation, bond cleavage, and mineralization to carbon dioxide, with the presence of nitrate ions accelerating the process through enhanced reaction rates with hydroxyl radicals derived from nitrate photolysis.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Chemistry, Organic
Xinyu Zhang, Qi Zhang, Linxuan Li, Shanshan Cao, Zhaohong Liu, Giuseppe Zanoni, Yongquan Ning, Yong Wu
Summary: An efficient method to prepare 3-functionalized oxetanes and azetidines has been realized by fluorocyclization, with the pendant electron-donating group playing a crucial role in the cyclization process. The strategy has been successfully applied for the first time to construct four-membered heterocycles, as confirmed by both DFT and experimental studies.
Article
Multidisciplinary Sciences
Jeffrey Y. K. Wong, Arunika I. Ekanayake, Serhii Kharchenko, Steven E. Kirberger, Ryan Qiu, Payam Kelich, Susmita Sarkar, Jianqian Li, Kleinberg X. Fernandez, Edgar R. Alvizo-Paez, Jiayuan Miao, Shiva Kalhor-Monfared, J. Dwyer John, Hongsuk Kang, Hwanho Choi, John M. Nuss, John C. Vederas, Yu-Shan Lin, Matthew S. Macauley, Lela Vukovic, William C. K. Pomerantz, Ratmir Derda
Summary: Peptide-based therapeutics with poor circulation half-life have been a challenge. In this study, researchers successfully selected albumin-binding macrocyclic peptides from genetically encoded libraries modified by specific chemistry. The selected peptides showed high affinity for human serum albumin and demonstrated longer in vivo circulation half-life, which is a promising starting point for developing compact macrocycles with extended half-life.
NATURE COMMUNICATIONS
(2023)
Article
Agriculture, Multidisciplinary
Paula Perez-Rodriguez, Anne-Desiree Schmitt, Sophie Gangloff, Jeremy Masbou, Gwenael Imfeld
Summary: The study found that leaching, dissipation, and degradation of pesticides in different types of soil mesocosms can be influenced by the planted or unplanted conditions, with planted mesocosms favoring pesticide degradation. Compound-specific stable isotope analysis showed that biodegradation of pesticides in soil-plant systems mainly occurred in the soil solution leached after rainfall events.
AGRICULTURE ECOSYSTEMS & ENVIRONMENT
(2021)
Article
Chemistry, Multidisciplinary
Ram Pratap Pandey, Mittali Maheshwari, Nazar Hussain
Summary: A Lewis-acid-mediated azidation of C2-substituted glycals with high regio- and stereoselectivity is described. This method offers excellent, scalable, and mild reaction conditions for introducing the azido group at the C3-position of various C2-substituted glycals. The electron-withdrawing nature of the C2-substituent is found to be crucial for the C3-selectivity. The installed azido group can be used for the synthesis of various C3-glycoconjugates and α-chiral azido naphthalene polyols.
CHEMICAL COMMUNICATIONS
(2023)
