Item – Theses Canada

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OCLC number
1006760926
Link(s) to full text
LAC copy
LAC copy
Author
Green, Anthony Laine,1976-
Title
The Directed ortho Metalation of pyridine derivatives with in situ boronation and links to the Suzuki-Miyaura cross coupling reaction.
Degree
M. Sc. -- Queen's University at Kingston, 2001
Publisher
Ottawa : National Library of Canada = Bibliothèque nationale du Canada, [2002]
Description
1 microfiche
Notes
Includes bibliographical references.
Abstract
The range of commercially available aryl boronic acids is increasing due to the popularity of the Suzuki-Miyauri cross coupling reaction. However, pyridyl boronic acids are of limited availability due to difficulties in preparation/isolation by conventional methods. The scope and application of a new method for the preparation pyridyl boronic acids has been shown. This method involved the Directed 'ortho' Metalation (D'o'M) of pyridine derivatives with 'in situ' boronation. This method has been used to prepare the following new pyridyl boronic acid derivatives: 3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carboxylic acid, N,N-Diethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinamide, N,N-Diethyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-isonicotinamide, 3-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine, 3-[1,3,6,2]Dioxazaborocan-2-yl-pyridine-2-carboxylic acid diethylamide, 4-[1,3,6,2]Dioxazaborocan-2-yl-N,N-diethyl-nicotinamide, 3-[1,3,6,2]Dioxazaborocan-2-yl-N,N-diethyl-isonicotinamide, Diethyl-carbamic acid 4-[1,3,6,2]dioxazaborocan-2-yl-pyridin-3-yl ester, 4-[1,3,6,2]Dioxazaborocan-2-yl-pyridine-3-sulfonic acid diethylamide, and 2-(3-Fluoro-pyridin-4-yl)-[1,3,6,2]dioxazaborocane. As an application, this methodology was linked to the Suzuki-Miyaura cross coupling reaction to produce the following new azabiaryl compounds: 3-Phenyl-pyridine-2-carboxylic acid diethylamide, N,N-Diethyl-3-phenyl-isonicotinamide, 3-Fluoro-4-phenyl-pyridine, N,N-Diethyl-4-(3-methoxy-phenyl)-nicotinamide, and N,N-Diethyl-4-thiophen-3-yl-nicotinamide.
ISBN
0612633101
9780612633100