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Synlett 1989; 1989(1): 25-27
DOI: 10.1055/s-1989-34687
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Stereodefined ß,ß-Disubstituted Vinylsilanes from the Silicon-Diverted Hydroboration of Alkynylsilanes and Palladium Chemistry

John A. Soderquist* , Juan C. Colberg
  • *Department of Chemistry, University of Puerto Rico, Rio Piedras, Puerto Rico 00931, USA
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Publication Date:
26 February 2002 (online)

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The novel (Z)-2-(9-borabicyclo[3.3.1]non-9-yl)-1- propenyl(triisopropyl)silane (1) is cleanly converted, with aryl and vinyl bromides, to the corresponding (E)-2-substituted 1-triiso-propylsilylpropenes 2 in high chemical yield (81-90%) and isomeric (>99%E) purity by the Suzuki reaction (catalysis with Pd(PPh3)4 in the presence of base).