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Synlett 1997; 1997(10): 1141-1142
DOI: 10.1055/s-1997-976
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Heck Reactions Starting from Silyl Enol Ethers - A Simple One-Pot Nonaflation-Coupling Procedure for the Synthesis of 1,3-Dienes

Matthias Webel, Hans-Ulrich Reissig*
  • *Institut für Organische Chemie der Technischen Universität Dresden, D-01062 Dresden, Germany, Fax: +49 351 463 7030, E-mail: Hans.Reissig@chemie.tu-dresden.de
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Publication History

Publication Date:
31 December 2000 (online)

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Starting from silyl enol ether 4 the corresponding alkenylnonaflate 5 was generated by treatment with nonafluorobutanesulfonyl fluoride (NfF) and a catalytic amount of tetra-n-butyl-ammonium fluoride (TBAF). By Pd-catalysis 5 was directly Heck-coupled with a variety of olefins to furnish functionalized 1,3-dienes 6 - 12. This one-pot procedure could be extended to other silyl enol ethers and provides new synthetic options.

silyl enol ethers - nonaflates - Heck reaction - palladium catalysis - 1,3-dienes