Journal
TETRAHEDRON
Volume 65, Issue 45, Pages 9233-9237Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.09.007
Keywords
Molecular iodine; 4-Hydroxycoumarin; Benzyl alcohol; Nucleophilic substitution; C-C bond formation
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Funding
- National Natural Science Foundation of China [20702047, J0830413]
- Natural Science Foundation of Zhejiang Province [R407106, Y4090028]
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A highly efficient method for the C-C bond formation via molecular iodine-catalyzed C3-alkylation reaction of 4-hydroxycoumarins with benzylic, benzhydrylic, allylic, and propargyl alcohols at 50 degrees C in MeNO2 is described. The 3-alkylated-4-hydroxycoumarins were obtained in good yields (up to 97%). By applying this reaction as the key step, a multi-substituted pyranocoumarin can easily be synthesized in a one-pot procedure. The advantages of this method are broad scope, mild conditions, and easy handling since water is the only side product. (C) 2009 Elsevier Ltd. All rights reserved.
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