Regiodivergent halogenation of (E)-β-chlorovinyl ketones via soft α-vinyl enolization strategy

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.