Palladium-catalyzed aryl amination-heck cyclization cascade: A one-flask approach to 3-substituted indoles

Abstract

(Chemical Equation Presented) Two for the price of one: A Pd/dppf-based catalyst provides access to the title compounds from 1,2-dihalogenated aromatic compounds and allylic amines in a single reaction flask. The initial aryl amination step occurs with excellent selectivity for the aryl iodide to ensure the formation of a single indole regioisomer, which can be functionalized in situ by N-arylation (see scheme). dba = dibenzylideneacetone, dppf = 1,1′-bis(diphenylphospanyl)ferrocene. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.