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Issue 39, 2018
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Electrophilic chloro(ω-alkoxy)lation of alkenes employing 1-chloro-1,2-benziodoxol-3-one: facile synthesis of β-chloroethers

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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.

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

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Publication details

The article was received on 11 Jul 2018, accepted on 17 Sep 2018 and first published on 26 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB01634H
Citation: Org. Biomol. Chem., 2018,16, 7203-7213
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    Electrophilic chloro(ω-alkoxy)lation of alkenes employing 1-chloro-1,2-benziodoxol-3-one: facile synthesis of β-chloroethers

    Y. Jia, L. Chen, H. Zhang, Y. Zheng, Z. Jiang and Z. Yang, Org. Biomol. Chem., 2018, 16, 7203
    DOI: 10.1039/C8OB01634H

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