Aromatic Ring-Opening of 2-Fluorobenzothiophenes by Alkyllithiums

Aromatic Ring-Opening of 2-Fluorobenzothiophenes by Alkyllithiums

Abstract Diphenylacetylenes are obtained when alkyllithium ­reagents are added to 3-aryl-2-fluorobenzothiophenes at low temperature. The aromatic ring-opening mechanism involves a nucleophilic addition of the alkyllithium to the sulfur atom of the thiophene. The resulting 2,2-diaryl-1-fluorovinyl an...

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Veröffentlicht in:Synlett 2005-02, Vol.2005 (2), p.247-250
Hauptverfasser: Belley, Michel, Douida, Zohra, Mancuso, John, De Vleeschauwer, Marc
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract Diphenylacetylenes are obtained when alkyllithium ­reagents are added to 3-aryl-2-fluorobenzothiophenes at low temperature. The aromatic ring-opening mechanism involves a nucleophilic addition of the alkyllithium to the sulfur atom of the thiophene. The resulting 2,2-diaryl-1-fluorovinyl anion subsequently undergoes a Fritsch-Buttenburg-Wiechell rearrangement to ­afford the diphenylacetylene.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2004-837230