Iron(III)-Mediated Bicyclization of 1,2-Allenyl Aryl Ketones: Assembly of Indanone-Fused Polycyclic Scaffolds and Dibenzo[<i>a</i>,<i>e</i>]pentalene Derivatives

Published on 2019-07-11T21:14:07Z (GMT) by
The 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[<i>a</i>,<i>e</i>]­pentalenes. Significantly, divergent synthetic applications have been achieved to provide densely functionalized polycyclic arrays.

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Miao, Maozhong; Jin, Mengchao; Chen, Panpan; Wang, Lei; Zhang, Shouzhi; Ren, Hongjun (2019): Iron(III)-Mediated Bicyclization of 1,2-Allenyl Aryl

Ketones: Assembly of Indanone-Fused Polycyclic Scaffolds and Dibenzo[a,e]pentalene Derivatives. ACS Publications. Collection.