6533b862fe1ef96bd12c6107
RESEARCH PRODUCT
Unusual redox play of Mo(V/IV) during oxidative aryl–aryl coupling
Siegfried R. WaldvogelSiegfried R. WaldvogelKristina Hackelöersubject
Aqueous solutionArylDimerOrganic ChemistryOxidative phosphorylationPhotochemistryBiochemistryRedoxMedicinal chemistryMetalchemistry.chemical_compoundchemistryvisual_artDrug Discoveryvisual_art.visual_art_mediumCyclohepteneOxidative coupling of methanedescription
The oxidative treatment of a suitable 1,3-diarylpropene precursor by MoCl5 causes a series of redox steps yielding a dimer of dibenzo[a,c]cycloheptene. After the oxidative aryl–aryl bond formation, a C,H activation occurs providing a tropylium intermediate. Upon aqueous workup the metal waste acts as reductive media generating the dimer in an almost quantitative manner. The oxidative generation of the tropylium species as well as the subsequent redox play by the metal waste is unique and unprecedented. The dimeric compound can be oxidatively cleaved and subsequently decarboxylated providing the key intermediate of a previous synthesis of metasequirin-B derivatives.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-03-01 | Tetrahedron Letters |