Base-Free Direct Synthesis of Alkynylphosphonates from Alkynes and H-Phosphonates Catalyzed by Cu₂O

Yanina Moglie*, Evangelina Mascaró, Victoria Gutierrez, Francisco Alonso and Gabriel Radivoy*

*Instituto de Química del Sur, INQUISUR (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, 8000 Bahía Blanca, Argentina, Email: gradivoycriba.edu.ar, ymoglieuns.edu.ar

Y. Moglie, E. Mascaró, V. Gutierrez, F. Alonso, G. Radivoy, J. Org. Chem., 2016, 81, 1813-1818.

DOI: 10.1021/acs.joc.5b02528

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Abstract

The reaction of various terminal alkynes with dialkyl phosphites in the presence of a catalytic amount of Cu₂O provides alkynylphosphonates in very good yields. Reactions are performed under air, in acetonitrile as solvent, and in the absence of base or ligand additives. This simple and mild methodology is compatible with a broad range of functional groups on the starting alkynes and can be scaled up to a gram scale.

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Key Words

phosphonates, oxygen

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ID: J42-Y2016