Regioselective Oxidative Arylation of Indoles Bearing N-Alkyl Protecting Groups: Dual C−H Functionalization via a Concerted Metalation−Deprotonation Mechanism
Journal of the American Chemical Society2010Vol. 132(41), pp. 14676–14681
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Shathaverdhan Potavathri, Kyle C. Pereira, Serge I. Gorelsky, Andrew Pike, Alexis P. LeBris, Brenton DeBoef
Abstract
The most direct method for synthesizing 2-arylindoles is oxidative coupling of an arene with an indole. We have shown that both the activity and regioselectivity of this cross-coupling reaction are correlated with the acidity of the medium. This insight has been applied to predict the best conditions for the oxidative cross-coupling of N-alkylindoles, an important class of substrates that has heretofore been incompatible with the harsh conditions required for oxidative cross-coupling. Both experimental and computational data indicate that the mechanism for C-H palladation of both the indoles and simple arenes is best described as concerted metalation-deprotonation, regardless of the substitution on the arene.
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