Date of Original Version
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.
Potavathri, S., Pereira, K. C., Gorelsky, S. I., Pike, A., LeBris, A. P., & DeBoef, B. (2010). Regioselective Oxidative Arylation of Indoles Bearing N-Alkyl Protecting Groups: Dual C−H Functionalization via a Concerted Metalation−Deprotonation Mechanism. J. Am. Chem. Soc., 132(41), 14676-14681. doi: 10.1021/ja107159b
Available at: https://doi.org/10.1021/ja107159b