Synthesis of 2-arylpiperidines by palladium couplings of aryl bromides with organozinc species derived from deprotonation of N-boc-piperidine |
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Authors: | Coldham Iain Leonori Daniele |
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Institution: | Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. i.coldham@sheffield.ac.uk |
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Abstract: | 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). The chemistry was applied to a very short synthesis of the alkaloid anabasine. |
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