LAUSR

Abstract On treating 2,4-dibromo-3,3,4,4-tetrafluorobut-1-ene, readily prepared from commercially available 4‑bromo-3,3,4,4-tetrafluorobut-1-ene (1), with 2.0 eq. of zinc-silver alloy at 40 °C in CH3CN, zinc insertion at the terminal C(sp3)–Br site proceeded selectively, giving the corresponding (3‑bromo-1,1,2,2-tetrafluorobut-3-en-1-yl)zinc bromide in high yield. This organozinc reagent was found to be thermally stable and easily handled. It was found that this organozinc reagent could participate in the cross-coupling reaction with various acyl chlorides or iodoarenes to give the corresponding CF2CF2-containing organic molecules in good yields. It was also revealed that Suzuki-Miyaura cross-coupling reactions at the C(sp2)–Br site of these CF2CF2-substituted products also proceeded in good to excellent yields.