1247072-49-6Relevant articles and documents
Regioselective oxidative arylation of indoles bearing N-alkyl protecting groups: Dual c-h functionalization via a concerted metalation-deprotonation mechanism
Potavathri, Shathaverdhan,Pereira, Kyle C.,Gorelsky, Serge I.,Pike, Andrew,Lebris, Alexis P.,Deboef, Brenton
, p. 14676 - 14681 (2010)
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.