Highly regioselective fluorination and iodination of alkynyl enolates.
A simple yet efficient approach to various functionalized quaternary alpha-alkynyl alpha-fluoro esters and gamma-iodoallenoates from readily available allenoates through an alkynyl enolate intermediate generated by LDA is presented. Reaction of this alkynyl enolate with NFSI gives the alpha-product (alpha-alkynyl-alpha-fluoro ester), whereas the reaction of the silyl ether of alkynyl enolate with I(2) gives solely the gamma-product (iodoallenoate).
Yang
Han
H
Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, USA.
Xu
Bo
B
Hammond
Gerald B
GB
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation
D000480:Alkynes