Synthesis of Dibenzo[a,d]cycloheptanoids via Aryne Insertion into 2-Arylidene-1,3-indandiones
A novel and unexpected aryne insertion cascade reaction on 2-arylidene-1,3-indandiones via conjugate addition of fluoride followed by formal C−C insertion is developed to afford dibenzo[a,d]cycloheptanoid derivatives in good yields with single isomer. This reaction represents a rare instance of cyclic enone C-C bond insertion (Acyl-Alkenylation) in aryne chemistry. Interestingly, 2-arylidene-1,3-indandiones bearing electron rich functional groups provided dibenz[a,c]anthracene-9,14-dione derivatives via [4 + 2] cycloaddition followed by ring expansion.
- This article is part of the themed collection: Synthetic methodology in OBC