Synthesis of 2-Arylpiperidines by Palladium Couplings of Aryl Bromides with Organozinc Species Derived from Deprotonation of N-Boc-Piperidine.

[摘要]：The organolithium species derived from proton abstraction of N-Boc-piperidine with s-BuLi and TMEDA can be transmetalated to the organozinc reagent, and this organometallic species can be coupled directly with aryl bromides in a Negishi-type reaction using palladium catalysis with the ligand tri-tert-butylphosphine (t-Bu3P-HBF4) to give title compds., e.g., I (R = Me, Cl, OMe, NH2). The chem. was applied to a very short synthesis of the alkaloid anabasine.

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