4.8 Article

Nanogold-Catalyzed cis-Silaboration of Alkynes with Abnormal Regioselectivity

Journal

ORGANIC LETTERS
Volume 16, Issue 5, Pages 1430-1433

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol500225x

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Funding

  1. project IRAKLEITOS II-University of Crete of the Operational Programme for Education and Lifelong Learning of the NSRF
  2. European Union (European Social Fund)
  3. National Resources

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The first example of gold-catalyzed silaboration of alkynes with PhMe(2)SiBpin is documented in the presence of supported gold nanoparticles. In the case of terminal alkynes, the reaction proceeds at ambient conditions in very good yields and the regioselectivity is opposite to that observed in the presence of Pd or Pt catalysts. The abnormal regioselectivity is attributed to steric factors imposed by the Au nanoparticle during the 1,2-addition of silylborane to the alkyne.

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