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Synfacts 2007(6): 0640-0640  
DOI: 10.1055/s-2007-968544
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Switching Between N- and O-Arylation of Aminoalcohols

Contributor(s): Paul Knochel, Tobias Thaler
A. Shafir, P. A. Lichtor, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
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Publikationsdatum:
22. Mai 2007 (online)

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Significance

Two complementary protocols for the Cu(I)-catalyzed N- and O-arylation of amino alcohols are presented. The properties of the catalyst are hereby directed by two different ligands which are assumed to either lower the electrophilicity of the Cu(I) center, thus favoring the coupling of the amino group, or to enhance its Lewis acidity leading to the preferential arylation of the alcohol.