Carbon-Carbon Bond Formation in Reactions of PhIO*HBF4/Silyl Enol Ether Adduct with Alkenes or Silyl Enol Ethers

Article abstract of DOI:10.1021/jo00272a028

A new method for generation of reactive α-ketomethyl aryliodonium intermediates from silyl enol ethers and PhIO*HBF4 has been developed.Reactions of PhIO*HBF4/silyl enol ether adduct with alkenes (1-hexene, cyclohexene, α-methylstyrene, allyltrimethylsilane, 2,3-dimethyl-2-butene) yielded products of allylic alkylation or (in case of 2,3-dimethyl-2-butene) a substituted dihydrofuran.Reactions of adducts from PhIO/HBF4 and silyl enol ethers of acetophone, p-chloroacetophenone, p-methylacetophenone, and p-nitroacetophenone with various silyl enol ethers led to unsymmetrical 1,4-butanediones as major products.