One-Pot Transformation of Ph2P(O)-Protected Ethynes: Deprotection Followed by Transition Metal-Catalyzed Coupling

Ph2P(O)-protected ethynes were successfully transformed to arylethynes in one-pot manner through t-BuOK-catalyzed deprotection followed by Sonogashira coupling with aryl halide. The arylethynes were obtained similarly by Ph2P(O)-deprotection, stannylation of the resulting terminal ethynes, and Migit...

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Veröffentlicht in:Journal of organic chemistry 2013-12, Vol.78 (24), p.12802-12808
Hauptverfasser: Peng, Lifen, Xu, Feng, Suzuma, Yoshinori, Orita, Akihiro, Otera, Junzo
Format: Artikel
Sprache:eng
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Zusammenfassung:Ph2P(O)-protected ethynes were successfully transformed to arylethynes in one-pot manner through t-BuOK-catalyzed deprotection followed by Sonogashira coupling with aryl halide. The arylethynes were obtained similarly by Ph2P(O)-deprotection, stannylation of the resulting terminal ethynes, and Migita-Kosugi-Stille coupling. Deprotection followed by intramolecular Eglinton coupling could be carried out in one-pot to provide cyclic butadiynes.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402176w