Electrophilic chloro(ω-alkoxy)lation of alkenes employing 1-chloro-1,2-benziodoxol-3-one: facile synthesis of β-chloroethers

Abstract

A four-component reaction for electrophilic chloro(ω-alkoxy)lation of alkenes has been described. The stable chloro-iodine(III) reagent and SOCl₂ were used as electrophilic and nucleophilic chlorine sources, respectively. This approach provides a straightforward way to synthesize various useful β-chloro ω-chloroalkyl ethers from a wide range of alkenes, including electron-deficient, aromatic and unactivated alkenes. The synthetic applications of this approach were also explored in some useful transformations.