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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.
Published Web Locationhttps://chemrxiv.org/articles/Dispersion-Controlled_Regioselective_Acid-Catalyzed_Intramolecular_Hydroarylation_of_cis-Methindolylstyrenes_to_Access_Tetrahydrobenzo_cd_indoles/7397492
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.