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Iron(III)-Mediated Bicyclization of 1,2-Allenyl Aryl Ketones: Assembly of Indanone-Fused Polycyclic Scaffolds and Dibenzo[a,e]pentalene Derivatives
journal contribution
posted on 2019-07-11, 21:14 authored by Maozhong Miao, Mengchao Jin, Panpan Chen, Lei Wang, Shouzhi Zhang, Hongjun RenThe
rapid construction of three-dimensional fused carbocycles is
a key challenge in synthetic chemistry. Herein, an unprecedented and
practical tandem Nazarov/oxidative umpolung 4π-ring closure
of readily available 1,2-allenyl aryl ketones mediated by iron(III)
chloride has been developed, furnishing a new family of indanone-fused
molecular architectures in moderate to excellent yields. The indanone-containing
blocks can be efficiently converted to unsymmetrical dibenzo[a,e]pentalenes. Significantly, divergent
synthetic applications have been achieved to provide densely functionalized
polycyclic arrays.
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Keywords
indanone-fusedunsymmetricalumpolungAllenyldibenzoHereinfurnishingIndanone-Fused Polycyclic Scaffoldsfunctionalized polycyclic arraysAssemblyBicyclizationNazarovallenylindanone-containing blocks4π-chloridepentalene DerivativesarylyieldconstructionArylapplicationclosurechallengeKetoneDibenzocarbocycleketonetandem
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