Sonogashira cross-coupling of (Z)-2‑bromo-2-CF3-vinyl benzyl sulfide and access to 4-CF3-3-iodo-2-substituted thiophenes

The Sonogashira cross-coupling reaction of (Z)-2‑bromo-2-CF3-vinyl benzyl sulfide with various terminal acetylenes afforded the corresponding (E)-2-CF3-1-buten-3-ynyl benzyl sulfides in good to high yields. Subsequent iodocyclization afforded the corresponding 4-CF3-3-iodo-2-substituted thiophenes in good to high yields. 1The CF3-containing thiophenes with various substituents were synthesized in a simple and convenient manner.2The Sonogashira cross-coupling of (Z)-2‑bromo-2-CF3-vinyl benzyl sulfide proceeded well affording the corresponding conjugated enyne sulfide.3(Z)-2‑bromo-2-CF3-vinyl benzyl sulfide was synthesized from 2-CF3-vinyl benzyl sulfide with excellent regio- and stereoselectivity in good yield. Sonogashira cross-coupling of (Z)-2‑bromo-2-CF3-vinyl benzyl sulfide and access to 4-CF3-3-iodo-2-substituted thiophenes Genki Ikeda, Mei Kawasaki, Takeshi Hanamoto* [Display omitted]