Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and <i>t</i>-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones
Pablo Macías-Benítez, Alfonso Sierra-Padilla, M. Jimenez-Tenorio, F. Javier Moreno‐Dorado, Francisco M. Guerra
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.
Topics & Concepts
ChemistryConjugated systemMicrowave irradiationKetoneTriple bondMedicinal chemistryCopperCatalysisMicrowaveDouble bondRing (chemistry)PhotochemistryOrganic chemistryPolymerPhysicsQuantum mechanicsSulfur-Based Synthesis TechniquesOrganophosphorus compounds synthesisCatalytic C–H Functionalization Methods