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.
The most direct method for synthesizing 2-arylindoles is oxidative coupling of ann class="Chemical">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: Domingo García-Cuadrado; Paula de Mendoza; Ataualpa A C Braga; Feliu Maseras; Antonio M Echavarren Journal: J Am Chem Soc Date: 2007-04-27 Impact factor: 15.419
Authors: Abhishek A Kantak; Shathaverdhan Potavathri; Rose A Barham; Kaitlyn M Romano; Brenton DeBoef Journal: J Am Chem Soc Date: 2011-11-16 Impact factor: 15.419
Authors: Gang Hong; Pradip D Nahide; Uday Kumar Neelam; Peter Amadeo; Arjun Vijeta; John M Curto; Charles E Hendrick; Kelsey F VanGelder; Marisa C Kozlowski Journal: ACS Catal Date: 2019-03-08 Impact factor: 13.084