Durham, Austin
(2024)
Metal-Mediated Propargylic C–H Functionalization of Alkynes.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
This is the latest version of this item.
Abstract
Herein is described the invention and development of several novel strategies for the transformation of simple alkynes into useful products via metal-mediated propargylic C–H functionalization. First a brief introduction into π-acid catalysis is presented in the context of allylic and propargylic functionalization, including the Wang group’s use and development of a substituted cyclopentadienyliron dicarbonyl species as a catalyst for propargylic hydroxyalkylation. Next is described the behavior of various organoiron intermediates from this system, and their use in other related organic transformations. Most notably among these are various cycloaddition processes for the production of densely substituted organoiron dihydropyrrolonyl- and dihyropyranyl- species that could be further transformed into organic products using divergent demetallation strategies. Next, ongoing efforts to leverage the stoichiometric intermediates for propargylic oxidation are presented in the context of reaction development. Finally, our initial discoveries with a related iridium-catalyzed system for propargylic C–H stannylation and germanylation are presented.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
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| Date: |
27 August 2024 |
| Date Type: |
Publication |
| Defense Date: |
1 December 2023 |
| Approval Date: |
27 August 2024 |
| Submission Date: |
5 April 2024 |
| Access Restriction: |
2 year -- Restrict access to University of Pittsburgh for a period of 2 years. |
| Number of Pages: |
350 |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
PhD - Doctor of Philosophy |
| Thesis Type: |
Doctoral Dissertation |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
C-H Functionalization, Catalysis, Organometallic, Cyclization |
| Date Deposited: |
27 Aug 2024 14:21 |
| Last Modified: |
27 Aug 2024 14:21 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/46465 |
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