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Nanogold-Catalyzed cis-Silaboration of Alkynes with Abnormal Regioselectivity

Charis Gryparis and Manolis Stratakis *

*Department of Chemistry, University of Crete, Voutes 71003 Iraklion, Greece, Email: stratakischemistry.uoc.gr

C. Gryparis, M. Stratakis, Org. Lett., 2014, 16, 1430-1433.

DOI: 10.1021/ol500225x



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Abstract

The presence of supported gold nanoparticles enables gold-catalyzed silaboration of terminal alkynes with PhMe2SiBpin. The reaction proceeds at ambient conditions in very good yields with a regioselectivity 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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Supported Gold Nanoparticle-Catalyzed cis-Selective Disilylation of Terminal Alkynes by σ Disilanes

C. Gryparis, M. Kidonakis, M. Stratakis, Org. Lett., 2013, 15, 6038-6041.


Key Words

vinylboronates, vinylsilanes


ID: J54-Y2014