Journal of the American Chemical Society 2008-08-06

Distinct reactivity of Pd(OTs)2: the intermolecular Pd(II)-catalyzed 1,2-carboamination of dienes.

Chris E Houlden, Chris D Bailey, J Gair Ford, Michel R Gagné, Guy C Lloyd-Jones, Kevin I Booker-Milburn

Index: J. Am. Chem. Soc. 130(31) , 10066-7, (2008)

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Abstract

A Pd-catalyzed intermolecular 1,2-carboamination route to indolines from N-aryl ureas and 1,3-dienes that proceeds under mild conditions in relatively nonacidic media, is presented. The in situ generation, or preformation, of a palladium tosylate emerges as a key parameter in gaining the requisite reactivity for the C-H insertion/carbopalladation/nucleophilic displacement process.