| Abstract
| - An efficient palladium-catalyzed cross-coupling reaction on heteroaromatic cations is described. Acomparative study of the Stille and Suzuki reactions shows that only the Stille reaction is able to producean efficient C−C bond formation between any of the four isomeric bromoquinolizinium bromides and avariety of stannanes. In the presence of the catalysts Pd(PPh3)4 or Pd2(dba)3P(o-Tol)3, vinyl, ethynyl,aryl, and heteroaryl groups are successfully incorporated into the quinolizinium system in satisfactoryyields under mild reaction conditions. This procedure represents a marked improvement on thefunctionalization of this class of heteroaromatic cation.
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