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

Steven B. Thorpe, 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/ol300575d (free Supporting Information)


Abstract

Using bis(pinacolato)diboron, catalytic amounts of CuII, and various amine bases in water under atmospheric conditions at rt, acyclic and cyclic α,β-unsaturated ketones and esters are β-borylated in good yield. Mechanistic investigations suggest that the role of the amine is not only to coordinate to CuII but also to activate a nucleophilic water molecule to form a reactive sp2-sp3 diboron complex.


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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

J. A. Calderone, W. L. Santos, Org. Lett., 2012, 14, 2090-2093.


Key Words

Borylation, Green Chemistry


ID: J54-Y2012-1110