Molecular iodine-catalyzed C3-alkylation of 4-hydroxycoumarins with secondary benzyl alcohols

作者：Lin Xufeng^*; Dai Xixiang; Mao Zhenjun; Wang Yanguang

来源：Tetrahedron, 2009, 65(45): 9233-9237.

DOI：10.1016/j.tet.2009.09.007

• Molecular iodine
• 4-Hydroxycoumarin
• Benzyl alcohol
• Nucleophilic substitution
• C-C bond formation

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 MeNO(2) 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.

• 出版日期2009-11-7
• 单位浙江大学