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

J Org Chem. 2021 Dec 3;86(23):16409-16424. doi: 10.1021/acs.joc.1c01763. Epub 2021 Oct 28.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes*
  • Catalysis
  • Copper
  • Cyclization
  • Microwaves
  • Phosphites*
  • tert-Butylhydroperoxide

Substances

  • Alkynes
  • Phosphites
  • Copper
  • tert-Butylhydroperoxide