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A Palladium-Catalyzed Strategy for the Preparation of Indoles: A Novel Entry into the Fischer Indole Synthesis

Seble Wagaw, Bryant H. Yang and Stephen L. Buchwald

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, Email: sbuchwalmit.edu

S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc., 1998, 120, 6621-6622.

DOI: 10.1021/ja981045r (free Supporting Information)


Abstract

Central to an alternative source of substrates for Fischer indolizations was a palladium-catalyzed coupling to prepare N-aryl benzophenone hydrazones. Hydrolysis of the hydrazones in the presence of ketones produced enolizable hydrazones that underwent Fischer indolization.

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Key Words

Fischer Indole Synthesis, Hydrazones, Indoles


ID: J48-Y1998-150