Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and -Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones.

J Org Chem

Departamento de Química Orgánica and Instituto de Biomoléculas, Universidad de Cádiz, Polígono Río San Pedro s/n, Puerto Real 11510, Cádiz, Spain.

Published: December 2021

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.1c01763DOI Listing

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