γ-halo-enones: A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles

Mei-Huey Lin; Yen Chih Huang; Chung Kai Kuo; Chang Hsien Tsai; Yi Syuan Li; Ting Chia Hu; Tsung Hsun Chuang

doi:10.1021/jo5001274

γ-halo-enones: A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles

Mei-Huey Lin, Yen Chih Huang, Chung Kai Kuo, Chang Hsien Tsai, Yi Syuan Li, Ting Chia Hu, Tsung Hsun Chuang

Department of Chemistry

Research output: Contribution to journal › Article

10 Citations (Scopus)

Abstract

A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered heterocyclic compounds.

Original language	English
Pages (from-to)	2751-2757
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	79
Issue number	6
DOIs	https://doi.org/10.1021/jo5001274
Publication status	Published - 2014 Mar 21

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All Science Journal Classification (ASJC) codes

Organic Chemistry

Cite this

Lin, M-H., Huang, Y. C., Kuo, C. K., Tsai, C. H., Li, Y. S., Hu, T. C., & Chuang, T. H. (2014). γ-halo-enones: A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles. Journal of Organic Chemistry, 79(6), 2751-2757. https://doi.org/10.1021/jo5001274

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abstract = "A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered heterocyclic compounds.",

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γ-halo-enones : A method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles. / Lin, Mei-Huey; Huang, Yen Chih; Kuo, Chung Kai; Tsai, Chang Hsien; Li, Yi Syuan; Hu, Ting Chia; Chuang, Tsung Hsun.

In: Journal of Organic Chemistry, Vol. 79, No. 6, 21.03.2014, p. 2751-2757.

Research output: Contribution to journal › Article

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10.1021/jo5001274