Straightforward Synthesis of Dihydrobenzofurans and Benzofurans from Arynes

Synthesis of dihydrobenzofurans was achieved by a route involving the insertion of arynes into formamides followed by trapping with zinc enolates of α-chlorinated methines. Benzofurans were generated from dihydrobenzofurans having a ketone group via the addition of an ethyl anion, the retro-aldol ty...

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Bibliographic Details
Published in:Organic letters 2013-08, Vol.15 (15), p.3938-3941
Main Authors: Yoshioka, Eito, Tanaka, Hidekazu, Kohtani, Shigeru, Miyabe, Hideto
Format: Article
Language:English
Subjects:
Benzofurans - chemical synthesis
Benzofurans - chemistry
Catalysis
Hydrocarbons, Cyclic - chemistry
Molecular Structure
Zinc - chemistry
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Summary:Synthesis of dihydrobenzofurans was achieved by a route involving the insertion of arynes into formamides followed by trapping with zinc enolates of α-chlorinated methines. Benzofurans were generated from dihydrobenzofurans having a ketone group via the addition of an ethyl anion, the retro-aldol type reaction, and the elimination of an amino group.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4017063