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One Step Synthesis of 4,6,8-Trimethoxyazulenes - a General Building Block for 2-Functionalized Azulenes.
Chemistry
January 2025
Ruprecht Karls Universitat Heidelberg, Organisch-Chemisches Institut, Im Neuenheimer Feld 270, 69120, Heidelberg, GERMANY.
Here we present a simple gold-catalyzed one-pot reaction of easily available diarylbutadiynes, with trimethoxybenzene as solvent and reactant to synthesize 4,6,8-trimethoxyazulenes. The methoxy substituents, which render the azulene very electron-rich, enable a change of azulenes typical regioselectivity for electrophilic substitutions, which enables facile electrophilic 2-substitution with iodine, bromine, chlorine, selenium or sulfur. Especially the 2-haloazulenes which can usually only be obtained through lengthy multistep syntheses are valuable building blocks for the synthesis of 2-substituted azulene derivatives.
View Article and Find Full Text PDFDMSO-promoted α-bromination of α-aryl ketones for the construction of 2-aryl-2-bromo-cycloketones.
Org Biomol Chem
January 2025
Laboratory of Chemical Biology, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin, 130022, China.
A DMSO-promoted practical one-step α-bromination reaction of α-aryl ketones with NBS has been developed for the construction of 2-aryl-2-bromo-cycloketones. The desired regioselective α-bromination products were isolated in moderate to good yields, with a maximum tested scale of 15 mmol. Notably, ketamine derivatives could be smoothly synthesized in two steps.
View Article and Find Full Text PDFOne-Step Process for the Regiodivergent Double Hydrocyanation of 1,3-Butadiene.
Angew Chem Int Ed Engl
December 2024
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, 2318 Yuhangtang Road, Hangzhou, 311121, P. R. China.
In industry, the two important nitrile starting materials, adiponitrile and 2-methylglutaronitrile, are primarily manufactured through the well-known DuPont process, which consists of a tandem sequence including first hydrocyanation, isomerization and second hydrocyanation. However, this mature process has the intrinsic defects of step efficiency and regioselectivity. Herein, we report a nickel-catalyzed divergent, one-step double hydrocyanation of 1,3-butadiene to produce either adiponitrile or 2-methylglutaronitrile in high regioselectivity.
View Article and Find Full Text PDFRegioselective Copolymerization of Glucose-Derived Allopyranoside Epoxide with Cyclic Anhydrides: Developing Precise Sugar-Functionalized Polyesters with Unique Altrose Linkages.
J Am Chem Soc
January 2025
Polymer Synthesis Laboratory, Laboratory, Chemistry Program, KAUST Catalysis Center, Physical Sciences and Engineering Division, King Abdullah University of Science and Technology (KAUST), Thuwal 23955, Saudi Arabia.
Article Synopsis
- Uniform sugar-functionalized polyesters merge sugar's diverse structure with biocompatibility and biodegradability, but irregular hydroxyl group placement has hindered their synthesis.
- A novel method using regioselective ring-opening copolymerizations (ROCOPs) allows for the creation of these polyesters with controlled properties and high glass transition temperatures, along with a pathway for producing valuable d-altrose through degradation.
- Mechanistic studies confirm the precise reactions involved, and the polyesters can be integrated into complex multiblock copolymers, enhancing their potential applications.
FON: An Innovative Fluorinated Group via Hydroetherification-Type Reactivity.
Org Lett
January 2025
Department of Chemistry, Brock University, St. Catharines, Ontario L2S 3A1, Canada.
An efficient strategy for preparing the novel -difluoroalkylhydroxylamine fluorinated functional group, coined FON, is reported. This analogue of medicinally important β-phenethyl ether scaffolds in uniting -difluoro and N-O moieties is synthesized in one step via chemo- and regioselectivity metal-free hydroetherification-type additions. As shown, this unique mode of reactivity is realized for a diverse substrate scope and applied to gram-scale synthesis and site-selective deuterium incorporation.
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