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J Am Chem Soc. 2010 Oct 20;132(41):14676-81. doi: 10.1021/ja107159b.

Regioselective oxidative arylation of indoles bearing N-alkyl protecting groups: dual C-H functionalization via a concerted metalation-deprotonation mechanism.

Author information

1
Department of Chemistry, University of Rhode Island, 51 Lower College Road, Kingston, Rhode Island 02881, USA.

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.

PMID:
20863119
PMCID:
PMC2954267
DOI:
10.1021/ja107159b
[Indexed for MEDLINE]
Free PMC Article

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