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

Abstract

Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu­(MeCN)4]­BF4 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.

Divergent Synthesis of (Benzo[b][1,4]diazepin‐2‐yl)phosphonates and (Quinoxalin‐2‐yl)methylphosphonates from Phosphoryl‐Substituted Conjugated Ynones

“…NMR spectrum of 4 a corresponds to literature data. [11] Diketone made without isolation reacted with o-phenylenediamine to give quinoxaline 5 a. Thus, the reaction of water addition to ynones 1 catalyzed by a carbene complex of gold and followed by the addition of o-phenylenediamine to the reaction medium can be considered as a new method for synthesis of phosphoryl-substituted quinoxalines.…”