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submitted on 29.11.2018 and posted on 29.11.2018by Xiao Cai, Anargul Tohti, Cristian Ramirez, Hassan Harb, Hrant Hratchian, Ben Stokes
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.