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
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container_title Synlett
container_volume 2005
creator Belley, Michel
Douida, Zohra
Mancuso, John
De Vleeschauwer, Marc
description 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.
doi_str_mv 10.1055/s-2004-837230
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