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Article
Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho-Substituted Benzylic Quaternary Centers
Organic Letters
  • Ryan G. Van Zeeland, Iowa State University
  • Levi M. Stanley, Iowa State University
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
8-1-2015
DOI
10.1021/acscatal.5b01272
Abstract
Palladium-catalyzed conjugate addition of arylboronic acids to β,β-disubstituted enones in aqueous media is reported. Additions of a wide range of arylboronic acids to β,β-disubstituted enones occur to form ketone products bearing benzylic all-carbon quaternary centers. These reactions are promoted by a simple catalyst prepared from palladium trifluoracetate and 2,2′-bipyridine. The use of aqueous sodium trifluoracetate as the reaction medium significantly enhances reactivity and enables the formation of challenging bis-benzylic and ortho-substituted benzylic all-carbon quaternary centers.
Comments

Reprinted (adapted) with permission from Organic Letters 5 (2015): 5203, doi:10.1021/acscatal.5b01272. Copyright 2015 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Ryan G. Van Zeeland and Levi M. Stanley. "Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to β,β-Disubstituted Enones in Aqueous Media: Formation of Bis-benzylic and ortho-Substituted Benzylic Quaternary Centers" Organic Letters Vol. 5 Iss. 9 (2015) p. 5203 - 5206
Available at: http://works.bepress.com/levi_stanley/4/