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

EVANGELINA MASCARÓ; GABRIEL RADIVOY; VICTORIA GUTIERREZ; YANINA MOGLIE; FRANCISCO ALONSO; EVANGELINA MASCARÓ; GABRIEL RADIVOY; VICTORIA GUTIERREZ; YANINA MOGLIE; FRANCISCO ALONSO

JOURNAL OF ORGANIC CHEMISTRY

American Chemical Society

Lugar: . Org. Chem. 2016, 81, 1813−1818; Año: 2016 vol. 81 p. 1813 - 1818

0022-3263

A simple and mild methodology for the direct synthesisof alkynylphosphonates is presented. The reaction of a variety ofterminal alkynes with dialkyl phosphites in the presence Cu2O (14 mol%) led to the formation of the corresponding alkynylphosphonates ingood to excellent yields. Reactions are performed under air, inacetonitrile as solvent, and in the absence of base or ligand additives.This new methodology is compatible with the presence of a widevariety of functional groups on the starting alkynes and can be scaledup to a gram scale.