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Synthesis 2000; 2000(7): 999-1003
DOI: 10.1055/s-2000-6292
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1-Methyl-1-vinyl- and 1-Methyl-1-(prop-2-enyl)silacyclobutane: Reagents for Palladium-Catalyzed Cross-Coupling Reactions of Aryl Halides

Scott E. Denmark* , Zhigang Wang
  • *Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA; Fax +1(217)3333984; E-mail: denmark@scs.uiuc.edu
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Publication Date:
31 December 2000 (online)

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1-Methyl-1-vinylsilacyclobutane (1) and 1-methyl-1-(prop-2-enyl)silacyclobutane (2) undergo rapid and high yielding cross-coupling with aromatic halides. Many different substituents and patterns on the aromatic moiety are tolerated. All reactions can be run at room temperature and require the presence of tetrabutylammonium fluoride and Pd(dba)2. Both silacyclobutanes can be made in one step from commercially available precursors.

cross-coupling - organosilicon - palladium catalysis - styrenes - alkenes

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