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Dispersion-Controlled Regioselective Acid-Catalyzed Intramolecular Hydroindolation of cis-Methindolylstyrenes To Access Tetrahydrobenzo[ cd]indoles.

  • Author(s): Cai, Xiao
  • Tohti, Anargul
  • Ramirez, Cristian
  • Harb, Hassan
  • Fettinger, James C
  • Hratchian, Hrant P
  • Stokes, Benjamin J
  • et al.

Published Web Location

https://pubs.acs.org/doi/10.1021/acs.orglett.9b00043
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Abstract

Readily prepared cis-β-(α',α'-dimethyl)-4'-methindolylstyrenes undergo acid-catalyzed intramolecular hydroindolation to afford 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 is preferred, apparently via concerted protonation and C-C bond formation. When dispersion is attenuated (by a substituent or heteroatom), regioselectivity erodes and competing oligomerization predominates for cis substrates. Similarly, all trans-configured substrates that we evaluated failed to cyclize efficiently.

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