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: ts
chem.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
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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
