Metal-Free Electrophilic Phosphination/Cyclization of Alkynes

Metal-Free Electrophilic Phosphination/Cyclization of Alkynes

A metal-free electrophilic phos­phin­ation reaction has been developed. Electro­philic phosphorus species generated in situ from secondary phos­phine oxides and Tf2O smoothly couple with alkynes possessing pendant nucleo­philes to afford the corresponding phos­phin­ated cyclization products in good...

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Veröffentlicht in:Journal of the American Chemical Society 2017-05, Vol.139 (17), p.6106-6109
Hauptverfasser: Unoh, Yuto, Hirano, Koji, Miura, Masahiro
Format: Artikel
Sprache:eng
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Zusammenfassung:A metal-free electrophilic phos­phin­ation reaction has been developed. Electro­philic phosphorus species generated in situ from secondary phos­phine oxides and Tf2O smoothly couple with alkynes possessing pendant nucleo­philes to afford the corresponding phos­phin­ated cyclization products in good yield. Preliminary NMR studies show that phos­phir­enium species may be involved as inter­mediates of the cyclization reactions.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b02977