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

• Published in: Tetrahedron Vol. 65; no. 45; pp. 9233 - 9237
• Main Authors: Lin, Xufeng, Dai, Xixiang, Mao, Zhenjun, Wang, Yanguang
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 07.11.2009; Elsevier
• Subjects: 4-Hydroxycoumarin; Benzyl alcohol; Chemistry; Chemistry, Organic; C–C bond formation; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Molecular iodine; Nucleophilic substitution; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Benzyl alcohol; Nucleophilic substitution; 4-Hydroxycoumarin; Molecular iodine; C–C bond formation; DOMINO REACTION; ROOM-TEMPERATURE; ONE-POT SYNTHESIS; CONVERSION; 1,3-DICARBONYL COMPOUNDS; EFFICIENT SYNTHESIS; MICHAEL ADDITION; FACILE SYNTHESIS; C-C bond formation; INHIBITORS; DERIVATIVES; Water; Catalytic reaction; Acetylenic compound; Mild operating conditions; Coumarine derivatives; Benzhydrol derivatives; Propargylic compound; Lactone; Oxygen heterocycle; Alkylation; Allylic compound; Nitromethane; Benzylic compound; Secondary alcohol; Chemical synthesis; Iodine
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2009.09.007

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 °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. [Display omitted]