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A copper-mediated oxidative coupling route to 3H- and 1H-indoles from N-aryl-enamines

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JournalEuropean Journal of Organic Chemistry
DateE-pub ahead of print - 13 Mar 2015
DatePublished (current) - Apr 2015
Issue number11
Volume2015
Number of pages4
Pages (from-to)2333-2336
Early online date13/03/15
Original languageEnglish

Abstract

A facile copper(II)-mediated C-H bond oxidation and C-C bond formation procedure has been applied to the synthesis of indole derivatives. Intramolecular oxidative coupling of 3,3-disubstituted enamines proceeded using a non-expensive and air-stable copper salt, Cu(2-ethylhexanoate)2, to afford the corresponding C-3 quaternary indolenine products in good to excellent yields. 1H-Indoles can be prepared in a similar manner but in this case, Cu(OAc)2·H2O has been found to be the preferred oxidant.

    Research areas

  • 1H-Indole, 3H-Indole, Copper-mediated coupling, Cyclization, Heterocycles

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