Efficient Heck Arylations of Cyclic and Acyclic Acrylate Derivatives Using Arenediazonium Tetrafluoroborates. A New Synthesis of the Antidepressant Drug (±)-Paroxetine

Abstract

[reaction: see text] The Heck arylation of acyclic- and cyclic-substituted acrylates using several arenediazonium tetrafluoroborates was investigated. Arylations were carried out under aerobic, ligand-free conditions to provide the corresponding substituted acrylates in moderate to high isolated yields. Heck arylations were usually completed in less than 2 h in refluxing methanol. The aza-endocyclic acrylate derivative 11a was converted into the antidepressant drug (+/-)-paroxetine in a concise new route in good overall yield.