Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons

The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were established for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields. The naphthannulation reaction of yne-allenone esters with β-ketonitriles provided new phenanth...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (74), p.1415-1418
Main Authors: Sha, Hong-Kai, Xu, Ting, Liu, Feng, Tang, Bu-Zheng, Hao, Wen-Juan, Tu, Shu-Jiang, Jiang, Bo
Format: Article
Language:English
Subjects:
Carboxylates
Chemical reactions
Cycloaddition
Esters
Organic chemistry
Phenanthrene
Polycyclic aromatic hydrocarbons
Reagents
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Summary:The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were established for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields. The naphthannulation reaction of yne-allenone esters with β-ketonitriles provided new phenanthrene-1-carboxylates via a base-mediated [2+2] cycloaddition/ring expansion sequence, whereas hitherto unreported tetracyclic tetrahydrotetraphene-7-carboxylates were obtained with good yield via a sequential double annulation cascade of yne-allenone esters with dimedone as a diphilic reagent. The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were developed for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc05018j