Base-Free Direct Synthesis of Alkynylphosphonates from Alkynes and H-Phosphonates Catalyzed by Cu2O
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Title: | Base-Free Direct Synthesis of Alkynylphosphonates from Alkynes and H-Phosphonates Catalyzed by Cu2O |
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Authors: | Moglie, Yanina | Mascaró, Evangelina | Gutiérrez, Victoria | Alonso, Francisco | Radivoy, Gabriel |
Research Group/s: | Nuevos Materiales y Catalizadores (MATCAT) |
Center, Department or Service: | Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica |
Keywords: | Synthesis | Alkynylphosphonates | Alkynes | H‑phosphonates | Cu2O |
Knowledge Area: | Química Orgánica |
Issue Date: | 3-Feb-2016 |
Publisher: | American Chemical Society |
Citation: | The Journal of Organic Chemistry. 2016, 81(5): 1813-1818. doi:10.1021/acs.joc.5b02528 |
Abstract: | A simple and mild methodology for the direct synthesis of alkynylphosphonates is presented. The reaction of a variety of terminal alkynes with dialkyl phosphites in the presence Cu2O (14 mol %) led to the formation of the corresponding alkynylphosphonates in good to excellent yields. Reactions are performed under air, in acetonitrile as solvent, and in the absence of base or ligand additives. This new methodology is compatible with the presence of a wide variety of functional groups on the starting alkynes and can be scaled up to a gram scale. |
Sponsor: | This work was generously supported by the Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET, PIP-2011-11220100100268), Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT, Préstamo BID PICT-2010-0669), and Universidad Nacional del Sur (UNS, PGI 24/Q044) from Argentina. V.G. thanks the CONICET for a postdoctoral fellowship. |
URI: | http://hdl.handle.net/10045/62753 |
ISSN: | 0022-3263 (Print) | 1520-6904 (Online) |
DOI: | 10.1021/acs.joc.5b02528 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 2016 American Chemical Society |
Peer Review: | si |
Publisher version: | http://dx.doi.org/10.1021/acs.joc.5b02528 |
Appears in Collections: | INV - MATCAT - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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2016_Moglie_etal_JOC_final.pdf | Versión final (acceso restringido) | 612,85 kB | Adobe PDF | Open Request a copy |
2016_Moglie_etal_JOC_rev.pdf | Versión revisada (acceso abierto) | 1,18 MB | Adobe PDF | Open Preview |
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