Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 46, Pages 10427-10432Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001373
Keywords
alcohols; carbocatalysis; dearomatization; graphene oxide; indole
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Funding
- University of Bologna
- PRIN-2017 project [2017W8KNZW]
- European Union [3881603]
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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.
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