Synthesis of 4-Arylpiperidines from 1-Benzyl-4-piperidone: Application of the Shapiro Reaction and Alkenylsilane Cross-Coupling

[reaction: see text] 1-Benzyl-3,4-unsaturated-4-piperidinyl benzyldimethylsilane has been prepared and observed to readily undergo palladium-catalyzed cross-coupling reactions with a variety of aryl iodides and aryl bromides to generate 3,4-unsaturated 4-arylpiperidines, often at ambient temperature.