Advantages of Organophosphorus Synthesis in Ionic Liquids: “Green” Approaches to Useful Phosphorus-Substituted Building Blocks

Abstract

Novel examples concerning the application of ionic liquids as a promoting reaction media in organophosphorus chemistry are discussed. Imidazolium ionic liquids were found to accelerate the Michaelis-Arbuzov reaction allowing to perform it under very mild conditions. Both phosphonium and imidazolium ILs give the possibility to perform easily direct amidation of phosphoryl acetic acids by various amines. Nucleophilic displacement reactionin a series of bromoalkylphosphonates was carried out in quantitative yield to afford azidoalkylphosphonates using the [bmim][PF₆]/H₂O system.

Keywords:

• 1,2,3-triazoles
• amidation
• azidoalkylphosphonates
• carbamoylmethyl phoshine oxides
• click chemistry
• ionic liquids
• nucleophilic displacement reactions
• the Michaelis-Arbuzov reaction

Acknowledgments

This work was supported by Russian Foundation of Basic Research (grants Nos.05-03-32692, 06-03-04003) and the Deutsche Forschungsgemeinschaft (DFG 436 RUS 113/766/0-1; 436 RUS 113/905/0-1).