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. [ABSTRACT FROM AUTHOR]