Efficient Heck arylations of cyclic and acyclic acrylate derivatives using arenediazonium tetrafluoroborates. A new synthesis of the antidepressant drug (+/-)-paroxetine.
[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.
Pastre
Julio Cezar
JC
Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, 13083-970, Campinas, São Paulo, Brazil.
Duarte Correia
Carlos Roque
CR
D000928:Antidepressive Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D003979:Diazonium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D017374:Paroxetine / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
D000928:Antidepressive Agents; D001881:Borates; D003979:Diazonium Compounds; D017374:Paroxetine