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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, Email: denmarkscs.uiuc.edu

S. E. Denmark, S. A. Tymonko, J. Am. Chem. Soc., 2005, 127, 8004-8005.

DOI: 10.1021/ja0518373 (free Supporting Information)


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Abstract

A mild, stereospecific cross-coupling of unsymmetrical 1,4-bissilyl-1,3-butadienes has been developed. A selective cross-coupling under mildly basic conditions afforded 4-aryl-1,3-dienylsilanes in excellent yield for a wide range coupling partners. The subsequent cross-coupling of the 4-aryl-1,3-dienylsilanes could be effected cleanly by the action of TBAF with electron-rich or electron-poor halides.

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Key Words

Hiyama Coupling, Hiyama-Denmark Coupling, 1,3-Dienes, Arenes


ID: J48-Y2005-2380