Sequential Cross-Coupling of 1,4-Bissilylbutadienes:  Synthesis of Unsymmetrical 1,4-Disubstituted 1,3-Butadienes

Scott E. Denmark* and Steven A. Tymonko
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801
J. Am. Chem. Soc., 2005, 127 (22), pp 8004–8005
DOI: 10.1021/ja0518373
Publication Date (Web): May 14, 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.

, denmark@scs.uiuc.edu

Abstract

Abstract Image

A mild and general and stereospecific cross-coupling reaction of unsymmetrical 1,4-bissilyl-1,3-butadienes has been accomplished. By the use of either a benzyldimethylsilyl or 2-thienyldimethylsilyl unit at one end of the dienylsilanol, a selective cross-coupling could be effected under mildly basic conditions (KOTMS) to afford 4-aryl-1,3-dienylsilanes in excellent yield for a wide range of aryl and alkenyl coupling partners. The second cross-coupling could be effected cleanly by the action of TBAF with electron-rich or electron-poor halides. The sequential process could be telescoped into a “one pot” procedure with overall excellent yields of the unsymmetrical 1,4-diaryl-1,3-butadienes.

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History

  • Published In Issue June 08, 2005
  • Received March 22, 2005

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