Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C–H Activation

A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles has been developed. This reaction relies on a norbornene-mediated cascade C–H activation process at the indole ring, which features high regioselectivity and excellent functional group tolerance. The reaction represents the first...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 133; no. 33; pp. 12990 - 12993
Main Authors Jiao, Lei, Bach, Thorsten
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.08.2011
Amer Chemical Soc
Subjects
Alkylation
Catalysis
Chemistry
Chemistry, Multidisciplinary
Indoles - chemistry
Norbornanes - chemistry
Palladium - chemistry
Physical Sciences
Science & Technology
FUNCTIONALIZATION
ROUTE
DIRECT ARYLATION
ELECTRON-WITHDRAWING SUBSTITUENTS
PROTECTING GROUP
ALKYL
OLEFINS
PYRROLES
SELECTIVITY
ALKENYLATION
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Summary:A palladium-catalyzed direct 2-alkylation reaction of free N-H indoles has been developed. This reaction relies on a norbornene-mediated cascade C–H activation process at the indole ring, which features high regioselectivity and excellent functional group tolerance. The reaction represents the first example for a generally applicable, direct C–H alkylation of indole at the 2-position.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja2055066