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Heck Coupling with Nonactivated Alkenyl Tosylates and Phosphates: Examples of Effective 1,2-Migrations of the Alkenyl Palladium(II) Intermediates

Anders L. Hansen, Jean-Philippe Ebran, Mårten Ahlquist, Per-Ola Norrby, Troels Skrydstrup*

*The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary, Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus, Denmark, Email: tschem.au.dk

A. L. Hansen, J.-P. Ebran, M. Ahlquist, P.-O. Norrby, T. Skydstrup, Angew. Chem. Int. Ed., 2006, 45, 3349-3353.

DOI: 10.1002/anie.200600442 (free Supporting Information)



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Abstract

The potential for nonactivated vinyl tosylates and phosphates to be worthy substrates for Heck couplings with electron-poor alkenes and styrene derivatives has been demonstrated. A mechanism for a 1,2-migration of the alkenyl palladium(II) intermediates is dicussed which leads to isomerized Heck products.

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Key Words

1,2-migration, alkenes, Heck reaction, phosphates, tosylates, 1,3-dienes


ID: J06-Y2006-1250