Two-Step Route to Indoles and Analogues from Haloarenes: A Variation on the Fischer Indole Synthesis

2011/10/06 by Martyn Inman, Anna Carbone, Christopher J. Moody · 3 citations
Chemistry · #Catalytic C–H Functionalization Methods #Asymmetric Synthesis and Catalysis #Catalytic Cross-Coupling Reactions

paper · doi:10.1021/jo201866c

Abstract

In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehydes or ketones under acidic conditions. The protocol, which is readily extended to the preparation of indole isosteres, 4- and 6-azaindoles and thienopyrroles, obviates the need to prepare potentially toxic aryl hydrazines, simultaneously avoiding undesirable anilines such as naphthylamines.

Cited by

• A visible-light-mediated oxidative C-N bond formation/aromatization cascade: photocatalytic preparation of N-arylindoles. [europepmc]
• N-heterocyclic-carbene-catalyzed synthesis of 2-aryl indoles. [europepmc]
• Understanding and Interrupting the Fischer Azaindolization Reaction. [europepmc]

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