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Expanding the Scope of Boronic Acid Catalysis: New and Improved Reactivity, Asymmetric Transformation

  • Author / Creator
    Ang, Hwee Ting
  • Catalysis is one of the 12 Principles of green chemistry and offers numerous advantages over the conventional stoichiometric chemical procedures, such as reduction of waste, better atom economy, and lower energy consumption. Furthermore, the ability to lower the activation energy allows direct transformations of previously non-reactive and inert compounds. In this context, boronic acid catalysis (BAC) has emerged as a versatile strategy for the direct functionalization of hydroxy and carbonyl-containing compounds, namely alcohols, carboxylic acids, polyols, and ketones, in a mild and selective manner. In the past decades, numerous transformations have been successfully adapted to BAC by many research groups worldwide. The astonishing accomplishments of BAC can be attributed to the beneficial physicochemical properties and the diversity of activation mechanisms offered by boronic acids. While great advances have been made in BAC, several challenges and limitations remain to be addressed. This thesis describes the efforts toward: (1) expanding the scope of reactions adaptable to BAC, such as the Beckmann rearrangement2 and the enantioselective desymmetrization of prochiral 1,3-diols, (2) improving the efficiency of existing BAC protocols for direct Friedel–Crafts benzylation of arenes with highly electron-deficient benzylic alcohols by using the strategy of co-catalysis, and (3) understanding the role of the boronic acid in these transformations to gain insights and guide the future advances in BAC.

  • Subjects / Keywords
  • Graduation date
    Fall 2021
  • Type of Item
    Thesis
  • Degree
    Doctor of Philosophy
  • DOI
    https://doi.org/10.7939/r3-8wq5-rs23
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.