Condensation of diethyl fluoromethylphosphonate with esters: An alternative synthetic route to diethyl α-fluoro-β-ketophosphonates

• Published in: Journal of fluorine chemistry Vol. 211; pp. 124 - 128
• Main Authors: Tarasenko, Karen V., Romanenko, Vadim D., Sorochinsky, Alexander E.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.07.2018; Elsevier; Elsevier BV
• Subjects: Aliphatic compounds; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Condensation; Dialkyl fluoromethylphosphonates; Esters; Ethylene; Fluoroketophosphonates; Nucleophilic addition; Phosphate mimics; Phosphates; Physical Sciences; Science & Technology; Triflate displacement; Fluoroketophosphonates; Triflate displacement; Dialkyl fluoromethylphosphonates; Phosphate mimics; Nucleophilic addition; ALPHA,BETA-UNSATURATED COMPOUNDS; ANALOGS; ALPHA,ALPHA-DIFLUORO-BETA-KETOPHOSPHONATES; (ALPHA-MONOFLUOROALKYL)PHOSPHONATES; CATALYTIC ENANTIOSELECTIVE FLUORINATION; KETO PHOSPHONATES; CHIRAL PALLADIUM COMPLEXES; INHIBITORS; DERIVATIVES; FLUOROALKYLPHOSPHONATES
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2018.04.014

[Display omitted] •Base-induced condensation of diethyl fluoromethylphosphonate with esters.•New method for preparation of racemic diethyl α-fluoro-β-ketophosphonates.•Method is operationally simple and general for aryl, heteroaryl, and alkyl esters. New general and operationally simple method for preparation of racemic diethyl α-fluoro-β-ketophosphonates has been developed. Addition of LDA to solution of diethyl fluoromethylphosphonate and aromatic, heteroaromatic and aliphatic esters in THF at −78 °C afforded the corresponding diethyl α-fluoro-β-ketophosphonates in good to high yields.