Boron Trifluoride Etherate Functioning as a Fluorine Source in an Iodosobenzene-Mediated Intramolecular Aminofluorination of Homoallylic Amines

Boron Trifluoride Etherate Functioning as a Fluorine Source in an Iodosobenzene-Mediated Intramolecular Aminofluorination of Homoallylic Amines

A widely used Lewis acid BF3·Et2O was shown to be capable of acting as an efficient fluorinating agent in an intramolecular aminofluorination reaction of homoallylic amines to provide 3-fluoropyrrolidines mediated by a commercially available hypervalent iodine(III) reagent PhIO at room temperature....

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Veröffentlicht in:Organic letters 2014-03, Vol.16 (5), p.1442-1445
Hauptverfasser: Cui, Jian, Jia, Qun, Feng, Ruo-Zhu, Liu, Shan-Shan, He, Tian, Zhang, Chi
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
Boranes - chemistry
Combinatorial Chemistry Techniques
Cyclization
Fluorine - chemistry
Iodobenzenes - chemistry
Lewis Acids - chemistry
Molecular Structure
Pyrrolidines - chemical synthesis
Pyrrolidines - chemistry
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Zusammenfassung:A widely used Lewis acid BF3·Et2O was shown to be capable of acting as an efficient fluorinating agent in an intramolecular aminofluorination reaction of homoallylic amines to provide 3-fluoropyrrolidines mediated by a commercially available hypervalent iodine(III) reagent PhIO at room temperature. A mechanism involving a carbocation intermediate was proposed on the basis of several experimental evidence.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500238k