Elsevier

Tetrahedron Letters

Volume 53, Issue 9, 29 February 2012, Pages 1048-1050
Tetrahedron Letters

Al(OTf)3: an efficient recyclable catalyst for direct nucleophilic substitution of the hydroxy group of propargylic alcohols with carbon- and heteroatom-centered nucleophiles to construct C–C, C–O, C–N and C–S bonds

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Abstract

A general and highly efficient Al(OTf)3-catalyzed methodology has been developed for the direct nucleophilic substitution of the hydroxy group in propargylic alcohols with a variety of carbon- and heteroatom-centered nucleophiles such as alcohols, aromatic compounds, amides, and thiols, leading to the construction of C–C, C–O, C–N and C–S bonds.

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Acknowledgment

Financial support by SASOL is gratefully acknowledged.

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  • Al(OTf)<inf>3</inf>-catalyzed one-pot synthesis of pyrrolo[3,2-d]pyrimidinedione derivatives

    2018, Tetrahedron Letters
    Citation Excerpt :

    Initially, the model reaction between 1,3-dimethyl-5-(methylamino)uracil (1a) and 1,3-di-phenylpropargyl alcohol (2a) was examined at reflux in the presence of Al(OTf)3. Since acetonitrile has been reported to be the solvent of choice for Al(OTf)3 catalysed reactions [15–17], it was selected for the current investigation. Based on previous results [15–17], substitution of the propargylic OH was envisaged to involve the soft carbon nucleophile of 1a and the soft electrophilic 1-position of the propargylic alcohol to yield propargylated uracil derivative 3aa (Scheme 1, Route A).

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