Synthesis of 2-arylpiperidines by palladium couplings of aryl bromides with organozinc species derived from deprotonation of N-boc-piperidine.
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.
Coldham
Iain
I
Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK. i.coldham@sheffield.ac.uk
Leonori
Daniele
D
D001555:Benzene Derivatives / Q000138:chemical synthesis*; D002712:Chlorides / Q000737:chemistry; D005563:Formic Acid Esters / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium; D010880:Piperidines / Q000138:chemical synthesis*; D017967:Zinc Compounds / Q000737:chemistry
D001555:Benzene Derivatives; D002712:Chlorides; D005563:Formic Acid Esters; D009942:Organometallic Compounds; D010880:Piperidines; D017967:Zinc Compounds; C434823:n-butyllithium; C000345:t-butyloxycarbonyl group; D010165:Palladium; C016837:zinc chloride