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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

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posted on 21.03.2014, 00:00 by Mei-Huey Lin, Yen-Chih Huang, Chung-Kai Kuo, Chang-Hsien Tsai, Yi-Syuan Li, Ting-Chia Hu, Tsung-Hsun Chuang
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.