Treatment of alkynes with diethyl phosphite and -butyl hydroperoxide in the presence of [Cu(MeCN)]BF under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding β-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate, producing eventually different phosphonylated indenones.
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http://dx.doi.org/10.1021/acs.joc.1c01763 | DOI Listing |
Org Biomol Chem
November 2024
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, Assam, India.
The quest for efficient and versatile methods for heterocycle synthesis continues to drive innovation in organic chemistry. In this context, the cyclization of alkynes catalyzed or mediated by boron trifluoride diethyl etherate (BF·OEt) has emerged as a powerful and widely applicable strategy. This review provides a comprehensive and authoritative overview of BF·OEt-catalyzed/mediated alkyne cyclization reactions, covering the scope, mechanisms, and applications of these processes.
View Article and Find Full Text PDFJ Org Chem
August 2024
College of Chemistry, International Phosphorus Laboratory, Zhengzhou University, Zhengzhou 450001, China.
A series of spiro-phosphonium compounds have been synthesized by copper-mediated coupling reaction of phosphacyclic compounds with alkynes. Their photophysical properties are tuned by varying substituents and exhibit different luminescent colors from blue to green, and finally, yellow. The fluorescence quantum efficiency of diethyl spiro-xanthenebenzophosphole in solid and liquid states reached 31% and 76%, respectively.
View Article and Find Full Text PDFRSC Adv
March 2024
WACKER-Chair of Macromolecular Chemistry, Catalysis Research Center, School of Natural Sciences, Department of Chemistry, Technical University of Munich Lichtenbergstraße 4 D-85748 Garching b. München Germany
A modular synthetic pathway for poly(diethyl vinylphosphonates) grafting-to gold nanoparticles is presented. Utilising an azide-dopamine derivative as nanoparticle coating agent, alkyne-azide click conditions were used to covalently tether the polymer to gold nanoparticles leading to stable and well distributed colloids for different applications.
View Article and Find Full Text PDFBeilstein J Org Chem
December 2023
Department of Basic and Applied Sciences for Engineering (SBAI), Sapienza University of Rome, via Castro Laurenziano, 7, 00161 Rome, Italy.
In order to replace the expensive metal/ligand catalysts and classic toxic and volatile solvents, commonly used for the hydration of alkynes, the hydration reaction of alkynes was studied in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate (BMIm-BF) adding boron trifluoride diethyl etherate (BF·EtO) as catalyst. Different ionic liquids were used, varying the cation or the anion, in order to identify the best one, in terms of both efficiency and reduced costs. The developed method was efficaciously applied to different alkynes, achieving the desired hydration products with good yields.
View Article and Find Full Text PDFMolecules
December 2023
Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, 1111 Budapest, Hungary.
The recovery and reuse of the enantioselective catalysts produced by tedious work are important not only from the perspective of green chemistry, but also from the point of view of productivity. Some of the carbohydrate-based crown ethers prepared in our research group were able to generate significant asymmetric induction in certain cases. However, they were not recoverable after the synthesis.
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