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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

Publisher

Western Washington University

OCLC Number

575037261

Digital Format

application/pdf

Genre/Form

Academic theses

Language

English

Rights

Copying of this thesis 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.

Included in

Chemistry Commons

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