title: Regioselective oxidative arylation of indoles bearing N-alkyl protecting groups: dual C-H functionalization via a concerted metalation-deprotonation mechanism.
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.
authors.affiliation: Department of Chemistry, University of Rhode Island, 51 Lower College Road, Kingston, Rhode Island 02881, USA.
authors.forename: Shathaverdhan
authors.initials: S
authors.lastname: Potavathri
authors.forename: Kyle C
authors.initials: KC
authors.lastname: Pereira
authors.forename: Serge I
authors.initials: SI
authors.lastname: Gorelsky
authors.forename: Andrew
authors.initials: A
authors.lastname: Pike
authors.forename: Alexis P
authors.initials: AP
authors.lastname: LeBris
authors.forename: Brenton
authors.initials: B
authors.lastname: DeBoef
mesh_terms: D007211:Indoles / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D010084:Oxidation-Reduction; D011522:Protons; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D008670:Metals; D011522:Protons