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