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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes: intramolecular capture of the vinyl-Au intermediate by the silicon electrophile.

The gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes 1 produced the corresponding 3-silylbenzo[b]thiophenes 2 in good to excellent yields. For example, the reaction of [2-(1-pentynyl)phenylthio]triisopropylsilane 1a, [2-(p-anisylethynyl)phenylthio]triisopropylsilane 1e, and [2-(phenylethynyl)phenylthio]triisopropylsilane 1g in the presence of 2 mol % of AuCl in toluene at 45 degrees C gave 2a, 2e, and 2g in 98, 99, and 97% yields, respectively. This reaction proceeds through intramolecular capture of the vinyl-Au intermediate by the silicon electrophile, so-called silyldemetalation.[1]

References

  1. Gold-catalyzed cyclization of (ortho-alkynylphenylthio)silanes: intramolecular capture of the vinyl-Au intermediate by the silicon electrophile. Nakamura, I., Sato, T., Terada, M., Yamamoto, Y. Org. Lett. (2007) [Pubmed]
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