Efficient Nucleophilic Addition to Haloacetylenes and Its Application

点击翻译按钮获取中文摘要

When imidazolines, imidazoles, N-allyl-, N-aryl-, or N-propyl-sulfonamides were heated with 1-halo-1-alkynes in DMF, cis-2-hetero groupsubstituted-1-halo-1-alkenes were produced with high regioand stereoselectivities. On treatmen with Pd catalysts, the sulfonamide adducts were led to pyrroles, indoles, and benzothiazine 1, 1-dioxides. Similarly, when amines or alcohols were heated with 1-halo-1-alkynes in DMF, their nucleophilic addition to 1-halo-1-alkynes resulted in the generation of vinyl carbene intermediates, which were intercepted with sodium sulfinate to give 2-hetero group-substituted-1-sulfonyl-1-alkenes.