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Date Permissions Signed
2-19-2010
Date of Award
2010
Document Type
Masters Thesis
Degree Name
Master of Science (MS)
Department
Chemistry
First Advisor
Clark, Timothy B. (Chemist)
Second Advisor
Vyvyan, James R.
Third Advisor
O'Neil, Gregory (Gregory W.)
Abstract
The versatility of the C-B bond in organic synthesis has led to extensive development of new methods for the selective incorporation of boron into organic substrates. The incorporation of boron substituents alpha to heteroatoms provides direct entry into substrates analogous to those formed and utilized in the Matteson homologation reaction. Our group has explored the diboration of various ketones using the (ICy)CuOt-Bu catalyst developed by Sadighi and co-workers. We found that (ICy)CuOt-Bu could be generated in situ using 3 mol % (ICy)CuCl and 5 mol% NaOt-Bu (Scheme 1). This catalyst system was shown to cleanly afford the diboration of various ketones in toluene at 50 °C over 2--22 hours. Treatment of the resulting products with SiO2 provides the corresponding α-hydroxyboronate esters. Products derived from aryl ketones are prone to decomposition during isolation via silica gel chromatography. Protection of alcohols has been achieved in a two step one flask procedure using TBSOTf. Matteson homologation products have been obtained in low yields by homologation of TBSprotected alcohols.
Type
Text
DOI
https://doi.org/10.25710/3v2y-fp65
Publisher
Western Washington University
OCLC Number
575037261
Subject – LCSH
Organocopper compounds; Copper catalysts; Organic compounds--Synthesis
Format
application/pdf
Genre/Form
masters theses
Language
English
Rights
Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this thesis for commercial purposes, or for financial gain, shall not be allowed without the author's written permission.
Recommended Citation
McIntosh, Melissa, "Copper-catalyzed diboration of ketones: facile synthesis of tertiary a-Hydroxyboronate esters" (2010). WWU Graduate School Collection. 36.
https://cedar.wwu.edu/wwuet/36