Synthesis of α-fluoroketones and α-fluoroenones in aqueous media

• Fluorination of α-bromoketones undergoes efficiently with TBAF·3H2O in water.
• Water as a reaction medium was superior to organic solvents for the fluorination.
• Condensation of α-fluoroketones with aldehydes affords α-fluoroenones.

An efficient synthesis of α-fluoroketones via the nucleophilic fluorination of α-bromoketones in water with TBAF·3H2O as the fluorinating agent was developed in this paper. In addition, a simple and efficient synthesis of α-fluoroenones through the condensation of α-fluoroketones with aldehydes promoted by sodium hydroxide in water was also discovered.

An efficient synthesis of α-fluoroketones via the nucleophilic fluorination of α-bromoketones in water with TBAF·3H2O as the fluorinating agent was developed in this paper. In addition, a simple and efficient synthesis of α-fluoroenones through the condensation of α-fluoroketones with aldehydes promoted by sodium hydroxide in water was also discovered.Figure optionsDownload as PowerPoint slide