Synthesis of diverse indole-containing scaffolds by gold(I)-catalyzed tandem reactions of 3-propargylindoles initiated by 1,2-indole migrations: scope and computational studies

Chemistry : a European Journal
Roberto SanzFélix Rodríguez

Abstract

Similar to propargylic carboxylates and sulphides, 3-propargylindoles undergo 1,2-indole migrations under cationic gold(I) catalysis. The intermediate Au-carbenoid complex may evolve through different pathways depending on the substituents at the propargylic and terminal positions of the alkyne moiety. Thus, 3-indenylindole derivatives were easily obtained through formal iso-Nazarov or Nazarov cyclizations. DFT computations support the formation of an alkylidenecyclopropane intermediate that undergoes gold-iso-Nazarov or gold-Nazarov cyclizations upon torquoselective ring opening. In addition, 3-dienylindoles could be accessed when none of the referred pathways were accessible and so the intermediate Au-carbenoid complex evolved via a 1,2-C-H insertion reaction. We have also demonstrated that the final products can be obtained in a one-pot protocol from easily available propargylic alcohols and indoles.

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Citations

Jan 6, 2015·Chemistry : a European Journal·Ana M SanjuánRoberto Sanz
Nov 10, 2013·Beilstein Journal of Organic Chemistry·Ana M SanjuánRoberto Sanz
Aug 2, 2011·Beilstein Journal of Organic Chemistry·Estela AlvarezRoberto Sanz
Jul 28, 2015·Chemistry : a European Journal·Estela ÁlvarezRoberto Sanz
Mar 12, 2019·The Journal of Organic Chemistry·Soniya Gandhi, Beeraiah Baire
Oct 23, 2012·Journal of the American Chemical Society·Joseph B Gianino, Brandon L Ashfeld
Apr 7, 2015·Chemical Reviews·Ruth Dorel, Antonio M Echavarren
Mar 3, 2018·The Journal of Organic Chemistry·Guilherme M MartinsClaudio C Silveira

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