Hydroxylation of unactivated tertiary carbon-hydrogen bonds using organic and metal-based catalysts
Abstract/Contents
- Abstract
- The selective hydroxylation of C--H bonds with complex substrates remains a grand challenge in modern synthetic chemistry. Selective methods for C--H oxidation have the potential to transform the field of natural product and complex molecule synthesis. While a variety of methods exist for the oxidation of C--H bonds, significant challenges in reaction efficiency, including catalyst turnover numbers and oxidant use, and positional selectivity still remain. One method that our laboratory has investigated for C--H hydroxylation uses 1,2,3-benzoxathiazine-2,2-dioxide-derived oxaziridines. By gaining an understanding of the off pathway processes that govern oxaziridine stability, significant improvements in reaction time, scope, and efficiency were obtained. Subsequent studies focused on elucidating the energetic requirements of the C--H bond oxidation event as well as probing the mechanism of the previously undescribed reduction of the oxaziridine intermediate in water and alcoholic solvents. The final chapter of this thesis details investigations into two metal-based approaches for catalyzing C--H hydroxylation, along with a comparative analysis of several methods for C--H hydroxylation that appear in the literature. These efforts serve to define the current scope and limitations of existing technologies for C--H hydroxylation and provide a reference for users of this technology.
Description
| Type of resource | text |
|---|---|
| Form | electronic; electronic resource; remote |
| Extent | 1 online resource. |
| Publication date | 2015 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Associated with | Adams, Ashley Margaret |
|---|---|
| Associated with | Stanford University, Department of Chemistry. |
| Primary advisor | Du Bois, Justin |
| Thesis advisor | Du Bois, Justin |
| Thesis advisor | Waymouth, Robert M |
| Thesis advisor | Wender, Paul A |
| Advisor | Waymouth, Robert M |
| Advisor | Wender, Paul A |
Subjects
| Genre | Theses |
|---|
Bibliographic information
| Statement of responsibility | Ashley Margaret Adams. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis (Ph.D.)--Stanford University, 2015. |
| Location | electronic resource |
Access conditions
- Copyright
- © 2015 by Ashley Margaret Adams
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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