TAJUDDIN, HAZMI (2013) New Strategies for Synthesis with Boronate Esters. Doctoral thesis, Durham University.
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Aryl and alkyl boronic acids and their derivatives have a broad variety of applications, ranging from uses in medicines to cross-coupling partners in modern organic synthesis. This thesis presents the work undertaken in both the synthetic and application aspects of this important class of synthetic intermediates.
Chapter 1 gives a brief overview on the bonding and physical properties of boronic acids, their synthesis and applications.
Chapter 2 shows that the activation of C-H bonds in the iridium-catalysed borylation of arenes is contingent on C-H acidity in the absence of steric effects, allowing for the prediction of regiochemistry through a simple 1H NMR analysis of the starting material.
Chapter 3 shows that the high electronic barrier hindering the borylation of C-H bonds alpha to a pyridyl nitrogen can be overcome through steric effects, and that the resultant α-pyridyl boronate can be used, in-situ, in Suzuki-Miyaura cross-coupling reactions.
Chapter 4 describes the development of C-H borylation/1,4-conjugate addition sequence, for the synthesis of β-aryl ketones and the corresponding alcohols under reducing conditions.
Chapter 5 describes the development of a new methodology for the preparation of alkyl boronate esters through copper-catalysed borylation of alkyl halides.
|Item Type:||Thesis (Doctoral)|
|Award:||Doctor of Philosophy|
|Keywords:||Borylation Conjugate Addition Arylboronates Alkylboronates Pyridines Iridium C-H Activation Copper pinacol ester boronic acid|
|Faculty and Department:||Faculty of Science > Chemistry, Department of|
|Copyright:||Copyright of this thesis is held by the author|
|Deposited On:||08 May 2013 15:10|