Divergent Halogenation Pathways of 2,2-Dichlorobut-3-yn-1-ols to 3-Chloro-4-Iodofurans and α-Chloro-γ-Iodoallenes: Electrophilic versus Pd(II)-Catalyzed Halogenation Strategies

초록

Divergent halogenation pathways of 2,2-dichlorobut-3-yn-1-ols have been developed to give 3,4-dihalofurans and 1,3-dihaloallenyl ketones in good to excellent yields. Thus, the readily accessible 2,2-dichlorobut-3-yn-1-ols were treated with the electrophilic halogen source to provide the 1,3-dihalogen-substituted allenyl ketones, whereas the use of Pd(II) catalyst promoted the oxypalladation followed by the electrophilic halogenation to give 3,4-dihalogen-substituted furan derivatives. The synthetic utility of 3,4-dihalofurans and 1,3-dihaloallenyl ketones is demonstrated in the sequential Suzuki cross coupling strategies.

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