Benzannulation
via Ruthenium-Catalyzed Diol–Diene
[4+2] Cycloaddition: One- and Two-Directional Syntheses of Fluoranthenes
and Acenes
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Abstract
A new benzannulation protocol is
described and applied to the synthesis
of polycyclic aromatic hydrocarbons. Ruthenium(0)-catalyzed diol–diene
[4+2] cycloaddition delivers cyclohex-1-ene-4,5-diols, which are subject
to aromatization upon dehydration or Nicholas diol deoxydehydration.
Employing diol and tetraol reactants, benzannulation can be conducted
efficiently in one- and two-directional modes, respectively, as illustrated
in the construction of substituted fluoranthenes and acenes