Efficient and Connective Assembly of Highly Functionalized Benzofurans Using o-Hydroxyphenones and Dichloroethylene

Efficient and Connective Assembly of Highly Functionalized Benzofurans Using o-Hydroxyphenones and Dichloroethylene

The preparation of highly functionalized benzofurans by a unique and connective transformation is reported. Base-catalyzed condensation of o-hydroxyphenones with 1,1-dichloroethylene generates the corresponding chloromethylene furans. These labile intermediates undergo a facile rearrangement into be...

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Veröffentlicht in:Organic letters 2012-03, Vol.14 (5), p.1298-1301
Hauptverfasser: Schevenels, Florian, Markó, István E
Format: Artikel
Sprache:eng
Schlagworte:
Benzofurans - chemistry
Catalysis
Dichloroethylenes - chemistry
Hydroxylation
Ketones - chemistry
Molecular Structure
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Zusammenfassung:The preparation of highly functionalized benzofurans by a unique and connective transformation is reported. Base-catalyzed condensation of o-hydroxyphenones with 1,1-dichloroethylene generates the corresponding chloromethylene furans. These labile intermediates undergo a facile rearrangement into benzofuran carbaldehydes under mild acidic conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300186s