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. 2014 Jun 6;16(11):2916-9.
doi: 10.1021/ol5010615. Epub 2014 May 27.

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

Fei Zhou  1 , Tom G Driver
Affiliations

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

Fei Zhou et al. Org Lett. .

Abstract

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.

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Figures

Scheme 1
Scheme 1. Current Challenges To Synthesizing 2-Substituted Aryl Azides
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