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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)


Abstract

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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Unexpected Copper(II) Catalysis: Catalytic Amine Base Promoted β-Borylation of α,β-Unsaturated Carbonyl Compounds in Water

S. B. Thorpe, J. A. Calderone, W. L. Santos, Org. Lett., 2012, 14, 1918-1921.


Key Words

Silylation, Green Chemistry


ID: J54-Y2012-1180