Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C−P Cross Coupling from <i>o</i>‐Hydroxyphenyl Enaminones and Phosphites
Dingsheng Cao, Jie‐Ping Wan, Yunyun Liu
Abstract
Abstract With an in situ C−H iodination tactic, a method for the synthesis of chromone‐3‐phosphonates was developed with trialkyl/triaryl phosphites as the reaction partners of o ‐hydroxyphenyl enaminones by palladium catalysis. The product formation consists of cascade C−H iodination, chromone annulation, and Arbuzov‐type C−P cross coupling as major transformations. In addition to providing an enaminone‐based synthetic method to chromone‐3‐phosphonates, the work shows the advantage of step economy by skipping the separate operation for preparing the iodo‐functionalized chromone intermediate.
Topics & Concepts
ChromoneChemistryHalogenationAnnulationPalladiumCatalysisMedicinal chemistryStereochemistryOrganic chemistryCombinatorial chemistrySynthesis of Organic CompoundsSulfur-Based Synthesis TechniquesOxidative Organic Chemistry Reactions