Regioselective Heck Couplings of α,β-Unsaturated Tosylates and Mesylates with Electron-Rich Olefins

Anders Lindhardt Hansen and Troels Skrydstrup*
Department of Chemistry and the Interdisciplinary Nanoscience Center, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark
Org. Lett., 2005, 7 (25), pp 5585–5587
DOI: 10.1021/ol052136d
Publication Date (Web): November 11, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ts@chem.au.dk

Abstract

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Highly regioselective Heck couplings of α,β-unsaturated tosylate and mesylate derivatives with N-acyl N-vinylamines and vinyl ethers were achieved. Several 2-alkoxy-1,3-dienes and 2-acylamino-1,3-butadienes were synthesized in good yields using 1.5 mol % of Pd2(dba)3, 3 mol % of DPPF, and diisopropylethylamine in dioxane. When working with α,β-unsaturated ketones and esters, this method provides a less costly alternative to similar couplings using a triflate electrophile.

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History

  • Published In Issue December 08, 2005
  • Received September 5, 2005

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