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Efficient synthesis of 3H-indoles enabled by the lead-mediated ?-arylation of ?-ketoesters or ?-lactams using aryl azides.

ABSTRACT: The development of a lead-mediated ?-arylation reaction between aryl azides and ?-ketoesters or ?-lactams that facilitates the formation of 3H-indoles is disclosed. Twenty-five examples are included which demonstrate the generality of this reaction to access aryl azides bearing tetrasubstituted o-alkyl substituents. When paired with a Staudinger reduction, this reaction streamlines the synthesis of functionalized 3H-indoles.

SUBMITTER: Zhou F

PROVIDER: S-EPMC4059265 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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Efficient synthesis of 3H-indoles enabled by the lead-mediated α-arylation of β-ketoesters or γ-lactams using aryl azides.

Zhou Fei F Driver Tom G TG

Organic letters 20140527 11

The development of a lead-mediated α-arylation reaction between aryl azides and β-ketoesters or γ-lactams that facilitates the formation of 3H-indoles is disclosed. Twenty-five examples are included which demonstrate the generality of this reaction to access aryl azides bearing tetrasubstituted o-alkyl substituents. When paired with a Staudinger reduction, this reaction streamlines the synthesis of functionalized 3H-indoles. ...[more]

PMID: 24865180

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