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Dispersion-Controlled Regioselective Acid-Catalyzed Intramolecular Hydroindolation of cis-Methindolylstyrenes To
Xiao Cai1, Anargul Tohti1, Cristian Ramirez1
1Department of Chemistry & Chemical Biology , University of California , 5200 North Lake Road , Merced , California 95343 , United States.
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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