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Dispersion-Controlled Regioselective Acid-Catalyzed Intramolecular Hydroarylation of cis-Methindolylstyrenes to Access Tetrahydrobenzo[cd]indoles

  • Author(s): Cai, Xiao
  • Tohti, Anargul
  • Ramirez, Cristian
  • Harb, Hassan
  • Hratchian, Hrant
  • Stokes, Ben
  • et al.
Abstract

Readily prepared cis-β-(α’,α’-dimethyl)-4’-methindolylstyrenes undergo Brønsted acid-catalyzed intramolecular hydroarylation to afford a variety of 3-aryl-5,5-dimethyl-1,3,4,5-tetrahydrobenzo[cd]indoles. Our experimental and computational investigations suggest that dispersive interactions between the indole and styrene preorganize substrates such that 6-membered ring formation occurs via a concerted hydroarylation step. When dispersability is attenuated (by a substituent or heteroatom), regioselectivity erodes and competing oligomerization predominates for cis substrates; all trans-configured substrates that we evaluated failed to cyclize efficiently.

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