Formation of substituted 1-naphthols and related products via dimerization of alkyl 3-(o-halo(het)aryl)-oxopropanoates based on a CuI-catalyzed domino C-arylation/condensation/aromatization process

Publikations-Art
Zeitschriftenbeitrag (peer-reviewed)
Autoren
Weischedel, H.; Sudheendran, K.; Mikhael, A.; Conrad, J.; Frey, W.; Beifuss, U.
Erscheinungsjahr
2016
Veröffentlicht in
Tetrahedron
Band/Volume
72/
DOI
10.1016/j.tet.2016.04.067
Seite (von - bis)
3454-3467
Abstract

Substrates bearing both a β-ketoester moiety and a (het)aryl halide structure element were dimerized to 1-naphthols and related products in the presence of catalytic amounts of CuI in isopropanol. The reaction starts with an intermolecular C-arylation, which is followed by an intramolecular condensation. The final aromatization delivers the highly substituted products with yields up to 81%.

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