Oxidative demetalation of cyclohexadienyl ruthenium(II) complexes: a net Ru-mediated dearomatization.
[reaction: see text] An experimentally simple method for the demetalation of spirocyclic cyclohexadienylruthenium(II) complexes has been developed. Treatment of an alkoxy-substituted cyclohexadienyl complex with CuCl(2) affords either azaspiro[4.5]decane derivatives or heavily functionalized tetrahydroisoquinolines. The former reaction manifold completes a net Ru-mediated dearomatization as the organometallic starting materials are prepared from (eta(6)-arene)Ru(II) precursors. Both of these heterocyclic products are well suited for further synthetic elaboration.
Pigge
F Christopher
FC
Department of Chemistry & Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri 63121-4499, USA. piggec@jinx.umsl.edu
Coniglio
John J
JJ
Rath
Nigam P
NP
D003300:Copper; D018360:Crystallography, X-Ray; D007546:Isoquinolines / Q000138:chemical synthesis; D008670:Metals / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D012428:Ruthenium / Q000737:chemistry*
D007546:Isoquinolines; D008670:Metals; D009942:Organometallic Compounds; C476923:cyclohexadienyl ruthenium; D003300:Copper; D012428:Ruthenium; C029892:cupric chloride