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; Webster L Santos

doi:10.1021/ol300618j

Copper(II)-catalyzed silyl conjugate addition to α,β-unsaturated conjugated compounds: Brønsted base-assisted activation of Si-B bond in water

Org Lett. 2012 Apr 20;14(8):2090-3. doi: 10.1021/ol300618j. Epub 2012 Apr 11.

Authors

Joseph A Calderone¹, Webster L Santos

Affiliation

¹ Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, USA.

PMID: 22494333
DOI: 10.1021/ol300618j

Abstract

A mild method for the installation of the dimethylphenylsilyl group on the β-carbon of electron-deficient olefins is reported. In the presence of a catalytic amount of copper(II) (1 mol %) and amine base (5 mol %) at rt, the transformation proceeds efficiently in water within 1.5-5 h to afford β-silylated products in yields of up to 90%.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkenes / chemistry*
Boron / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Copper / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Organosilicon Compounds / chemical synthesis*
Organosilicon Compounds / chemistry*
Water

Substances

Alkenes
Organometallic Compounds
Organosilicon Compounds
Water
Copper
Boron