One-Pot Synthesis of Trisubstituted Conjugated Dienes via Sequential Suzuki−Miyaura Cross-Coupling with Alkenyl- and Alkyltrifluoroborates

Gary A. Molander*† and Yasuo Yokoyama†‡;
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, and Department of Chemistry, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan
J. Org. Chem., 2006, 71 (6), pp 2493–2498
DOI: 10.1021/jo052636k
Publication Date (Web): February 15, 2006
Copyright © 2006 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.

,
†

 University of Pennsylvania.

,
‡

 Sophia University.

, gmolandr@sas.upenn.edu, ; , yasuo-y@sophia.ac.jp

Abstract

Abstract Image

The sequential, stereoselective disubstitution of 1,1-dibromoalkenes using a variety of alkenyltrifluoroborates followed by alkyltrifluoroborates in the presence of Pd(PPh3)4 is described. This synthetic method proceeds smoothly in one pot under mild reaction conditions to provide the corresponding trisubstituted, conjugated dienes in excellent yield. Moreover, the method is operationally very simple because the organotrifluoroborates are stable in air, and the byproducts are innocuous inorganic salts.

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History

  • Published In Issue March 17, 2006
  • Received December 22, 2005

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