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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Financial support by SASOL is gratefully acknowledged.
References and notes (14)
Tetrahedron
(2002)et al.Eur. J. Org. Chem.
(2011)Sci. Synth.
(2002)et al.Chem. Commun.
(2004)et al.J. Org. Chem.
(2007)et al.Adv. Synth. Catal.
(2007)et al.Chem. Eur. J.
(2010)- et al.
J. Am. Chem. Soc.
(2000)et al.J. Am. Chem. Soc.
(2001)et al.J. Am. Chem. Soc.
(2002)et al.J. Am. Chem. Soc.
(2002)et al.J. Am. Chem. Soc.
(2003)et al.J. Am. Chem. Soc.
(2003)et al.J. Am. Chem. Soc.
(2003)et al.Angew. Chem., Int. Ed.
(2003)et al.Org. Lett.
(2004)et al.Chem. Eur. J.
(2005)et al.Org. Lett.
(2005)et al.Tetrahedron
(2009)et al.Tetrahedron Lett.
(2010)et al.J. Org. Chem.
(2010) - et al.
Tetrahedron
(2000)et al.Chem. Commun.
(2006)et al.J. Org. Chem.
(2006)et al.Synlett
(2006)et al.Tetrahedron Lett.
(2006)et al.Adv. Synth. Catal.
(2011) - et al.
Eur. J. Org. Chem.
(2006)et al.J. Org. Chem.
(2009) - et al.
Tetrahedron Lett.
(1995)et al.J. Org. Chem.
(2000)et al.Org. Lett.
(2006)et al.J. Org. Chem.
(2006)et al.Angew. Chem., Int. Ed.
(2008)et al.J. Am. Chem. Soc.
(2010)et al.Synlett
(2011) - et al.
Org. Lett.
(2010)et al.Tetrahedron Lett.
(2007)et al.Synth. Commun.
(2008)
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2018, Tetrahedron LettersCitation 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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