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* and Kevin I. Booker-Milburn*

*School of Chemistry, Cantock's Close, University of Bristol, Bristol, BS8 1TS, U.K., Email: k.booker-milburnbristol.ac.uk, guy.lloyd-jonesbristol.ac.uk

C. E. Houlden, C. D. Bailey, J. G. Ford, M. R. Gagné, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc., 2008, 130, 10066-10067.

DOI: 10.1021/ja803397y

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Abstract

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

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Key Words

Indolines, Benzoquinone

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ID: J48-Y2008-2080