Efficient Heck arylations of cyclic and acyclic acrylate derivatives using arenediazonium tetrafluoroborates. A new synthesis of the antidepressant drug (+/-)-paroxetine

Org Lett. 2006 Apr 13;8(8):1657-60. doi: 10.1021/ol060248e.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antidepressive Agents / chemical synthesis*
  • Antidepressive Agents / pharmacology
  • Borates / chemistry*
  • Catalysis
  • Diazonium Compounds / chemistry*
  • Molecular Structure
  • Paroxetine / chemical synthesis*
  • Paroxetine / pharmacology
  • Stereoisomerism

Substances

  • Antidepressive Agents
  • Borates
  • Diazonium Compounds
  • Paroxetine