title: Regiodivergent halogenation of (E)-β-chlorovinyl ketones via soft α-vinyl enolization strategy.
abstract: The soft α-vinyl enolization of (E)-β-chlorovinyl ketones was investigated in the presence of various halogen electrophiles. Depending on the nature of halogen electrophiles, the selective formation of three products, namely α,α-dichloropropargyl ketones, α,γ-dihaloallenyl ketones, and 3-halofurans, was observed. The observed regiodivergent nucleophilic pathways of (E)-β-chlorovinyl ketones demonstrate the diversity-oriented synthesis strategy in which the nucleophilic reactivity of (E)-β-chlorovinyl ketones can be selectively modulated by the choice of suitable hard and soft electrophiles.
authors.affiliation: College of Pharmacy, Chung-Ang University , 84 Heukseok-ro, Dongjak, Seoul 156-756, Republic of Korea.
authors.forename: Hun Young
authors.initials: HY
authors.lastname: Kim
authors.forename: Seokwoo
authors.initials: S
authors.lastname: Lee
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Kyungsoo
authors.initials: K
authors.lastname: Oh
mesh_terms: D002384:Catalysis; D054879:Halogenation; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D006843:Hydrocarbons, Chlorinated; D006846:Hydrocarbons, Halogenated; D007659:Ketones; D014753:Vinyl Compounds; C587802:dichlorovinyl ketone