The solid-phase Nicholas reaction: Scope and limitations

Journal article, 2005

Two libraries of α-substituted alkynes has been prepared on solid phase using a sequential Sonogashira/ Nicholas reaction approach. The scope of nucleophiles in the Nicholas reaction on solid phase has been investigated, including carbon, oxygen, nitrogen, sulfur, fluoride, and hydride nucleophiles. The conditions for the reaction sequence have been optimized in terms of Lewis acid, catalyst for the Sonogashira step, temperature, reaction time, and decomplexation method, enabling the five-step sequence to be performed in 1 day. © 2005 American Chemical Society.