PhI(OCOCF3)2-catalyzed nucleophilic substitution of aromatic propargyl alcohols

Hypervalent [bis(trifluoroacetoxy)iodo]benzene (PIFA) is shown to behave as a Lewis acid for the nucleophilic substitution of propargylic alcohols with diverse C-, O-, S-, and N-nucleophiles without the synergistic assistance of other acid activators or stoichiometric oxidants, while fully demonstra...

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Bibliographic Details
Published in:Tetrahedron 2015-04, Vol.71 (17), p.2549-2554
Main Authors: Weng, Shiue-Shien, Hsieh, Kun-Yi, Zeng, Zih-Jian
Format: Article
Language:English
Subjects:
[Bis(trifluoroacetoxy)iodo]benzene
Hypervalent iodine(III)
Nucleophilic substitution of propargylic alcohols
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Summary:Hypervalent [bis(trifluoroacetoxy)iodo]benzene (PIFA) is shown to behave as a Lewis acid for the nucleophilic substitution of propargylic alcohols with diverse C-, O-, S-, and N-nucleophiles without the synergistic assistance of other acid activators or stoichiometric oxidants, while fully demonstrating a complementary utility of oxidative hypervalent iodine(III) in terms of its high reactivity in the coupling reactions of propargyl alcohols with allyl trimethylsilane and electron-rich arenes. A propargylic carbocation generated by a reversible equilibrium between the reaction substrates and PIFA catalyst is involved in the reaction mechanism as revealed by the reaction parameters and control experiments. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.03.013