Synthesis of indoles with a polyfluorinated benzene ring

Synthesis of indoles with a polyfluorinated benzene ring

A two-step sequence consisting of a Sonogashira coupling of polyfluorinated 2-iodoanilines with terminal alkynes, followed by a KOH promoted cyclization of the 2-alkynylanilines thus formed, has been developed as a one-pot synthesis of 2-R-indoles (R=n-Bu, Ph, CH2OTHP→CH2OH, C(CH3)2OH→H) containing...

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Veröffentlicht in:Tetrahedron 2013-09, Vol.69 (39), p.8477-8486
Hauptverfasser: Politanskaya, Larisa V., Chuikov, Igor P., Shteingarts, Vitalij D.
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes
Benzene
Coupling reactions
Cyclization of polyfluorinated ortho-alkynylanilines
Indoles
Joining
One-pot synthesis
Polyfluorinated indoles
Synthesis
Terminals
Tetrahedrons
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Beschreibung
Zusammenfassung:A two-step sequence consisting of a Sonogashira coupling of polyfluorinated 2-iodoanilines with terminal alkynes, followed by a KOH promoted cyclization of the 2-alkynylanilines thus formed, has been developed as a one-pot synthesis of 2-R-indoles (R=n-Bu, Ph, CH2OTHP→CH2OH, C(CH3)2OH→H) containing a polyfluorinated benzene moiety. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.07.037