• 文献标题:   Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode
  • 文献类型:   Article
  • 作  者:   LOMBARDI L, BELLINI D, BOTTONI A, CALVARESI M, MONARI M, KOVTUN A, PALERMO V, MELUCCI M, BANDINI M
  • 作者关键词:   alcohol, carbocatalysi, dearomatization, graphene oxide, indole
  • 出版物名称:   CHEMISTRYA EUROPEAN JOURNAL
  • ISSN:   0947-6539 EI 1521-3765
  • 通讯作者地址:   Alma Mater Studiorum Univ Bologna
  • 被引频次:   1
  • DOI:   10.1002/chem.202001373 EA JUL 2020
  • 出版年:   2020

▎ 摘  要

The site-selective allylative and allenylative dearomatization of indoles with alcohols was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt % loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 degrees C, 6 h), broad substrate scope (33 examples, yield up to 92 %) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented.