A Free-Radical Cascade Trifluoromethylation/Cyclization of N‑Arylmethacrylamides and Enynes with Sodium Trifluoromethanesulfinate and Iodine Pentoxide

A Free-Radical Cascade Trifluoromethylation/Cyclization of N‑Arylmethacrylamides and Enynes with Sodium Trifluoromethanesulfinate and Iodine Pentoxide

An I2O5-promoted free-radical cascade trifluoromethylation/cyclization of a broad range of N-arylmethacrylamides and enynes with sodium trifluoromethanesulfinate in aqueous medium has been achieved. This strategy allows highly selective access to a variety of CF3-containing oxindoles and pyrrolidine...

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Veröffentlicht in:Organic letters 2014-07, Vol.16 (14), p.3688-3691
Hauptverfasser: Zhang, Lizhi, Li, Zejiang, Liu, Zhong-Quan
Format: Artikel
Sprache:eng
Schlagworte:
Acrylamides - chemistry
Alkynes - chemistry
Catalysis
Cyclization
Electron Spin Resonance Spectroscopy
Free Radicals
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Iodine Compounds - chemistry
Molecular Structure
Oxides - chemistry
Oxindoles
Sodium - chemistry
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Beschreibung
Zusammenfassung:An I2O5-promoted free-radical cascade trifluoromethylation/cyclization of a broad range of N-arylmethacrylamides and enynes with sodium trifluoromethanesulfinate in aqueous medium has been achieved. This strategy allows highly selective access to a variety of CF3-containing oxindoles and pyrrolidines. Electron spin resonance (ESR) studies indicate that atom-transfer processes are involved in this system.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5014747