Copper(II)-Catalyzed Silyl Conjugate Addition to α,β-Unsaturated Conjugated Compounds: Brønsted Base-Assisted Activation of Si-B Bond in Water
Joseph A. Calderone and Webster L. Santos*
*Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, United States, Email: santoswvt.edu
J. A. Calderone, W. L. Santos, Org. Lett., 2012, 14, 2090-2093.
DOI: 10.1021/ol300618j (free Supporting Information)
The presence of a catalytic amount of copper(II) and an amine base enables a mild method for the installation of the dimethylphenylsilyl group on the β-carbon of electron-deficient olefins at rt. The transformation proceeds efficiently in water within 1.5-5 h to afford β-silylated products in good yields.
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S. B. Thorpe, J. A. Calderone, W. L. Santos, Org. Lett., 2012, 14, 1918-1921.