Three-Component Direct Phosphorylation of Aldehydes and Alkylation of Ketones: Synthesis of γ-Ketophosphine Oxides under Acidic Conditions

An effective and economical acid-promoted three-component reaction for the construction of C-P and C-C bonds for the synthesis of gamma-ketophosphine oxides with water as the only byproduct was developed. Detailed mechanistic experiments confirmed that the reaction proceeds by phospha-aldol elimination, in which a benzylic carbocation is generated from the phosphorylation of aldehydes, which then reacts with ketone enolates under acidic conditions.

Automated summary

In this study, an effective and economical acid-promoted three-component reaction was developed for the synthesis of gamma-ketophosphine oxides, which involves the construction of C-P and C-C bonds with water as the only byproduct. Mechanistic experiments confirmed that the reaction proceeds through phospha-aldol elimination.