Group IX Metal-Catalyzed C–H Activation Towards the Development of New Synthetic Strategies Restricted; Files & ToC
Hollerbach, Michael (Summer 2023)
Published
Abstract
Part 1 of this dissertation describes efforts leading to the development of a new class of chiral dienes, specifically C2 symmetric cyclooctadienes (CODs). Proven to be formidable ligands for asymmetric catalysis in recent years these ligands were limited to 1,5 disubstituted scaffolds historically. Through collaboration with the Davies Group at Emory University, previously unreported 3,7 disubstituted CODs were accessed in one step and subsequently diversified. The in-situ development of a homogeneous rhodium catalyst with these ligands for enantioselective C(sp3)–H functionalization is described.
Part 2 of this dissertation addresses efforts to provide modern small molecule discovery with novel heterocyclic moieties for new cutting-edge agrochemicals and pharmaceuticals. Leveraging late-stage functionalization of C–H bonds has become increasingly powerful to target these moieties, however, non-directed activation of desired C–H bonds remain challenging. In response to this limitation, the design and use of directing groups has become extremely important despite their shortcomings. Previously, oxidative addition has been employed for directed annulations, but analogous reactivity with transmetallation has remained underexplored. Currently, we have developed new methodology to leverage transmetallation of boryl species to promote distal C(sp2)–H activation and subsequent functionalization.
Part 3 of this dissertation describes the effort of the Blakey Lab to adopt and pioneer new sustainable and green processes in the chemistry lab. Through continual commitment to reducing our environmental and carbon footprints, the Blakey lab has changed how we fundamentally operate day-to-day to lower or resource consumption and extend the life our consumables. This has led to several invaluable advancements in the understanding of energy consumption, water usage and waste production. Furthermore, quantitative data was collected to highlight the benefit for investing in new heat/stir plates and aluminum heating blocks.
Table of Contents
This table of contents is under embargo until 16 August 2025
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File download under embargo until 16 August 2025 | 2023-07-03 10:23:53 -0400 | File download under embargo until 16 August 2025 |
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