A natural side-process to this reaction is a Glaser coupling, and it directly superceded the Castro-Stephens reaction, one of whose catalysts this process generates in situ.
This reaction is the terminal step of the Miller synthesis of the natural product harveynone, and one difficulty in elucidating its mechanism lies in explaining how one reagent might be deprotonated by a base as weak as triethylamine. A natural side-process to this reaction is a Glaser coupling, and it directly superceded the Castro-Stephens reaction, one of whose catalysts this process generates in situ. This reaction, whose rate-limiting step is a transmetallation that links its two catalytic cycles, allows alkynes to trade a terminal hydrogen for an R-group on an aryl or vinyl halide. For 10 points, name this palladium-catalyzed modification of the Castro-Stephens reactions.
This reaction is the terminal step of the Miller synthesis of the natural product harveynone, and one difficulty in elucidating its mechanism lies in explaining how one reagent might be deprotonated by a base as weak as triethylamine.
{Sonogashira} coupling