Palermo, Philip
(2023)
Mechanistic Insights into Iron-Catalyzed Allenic C–H Functionalization.
Master's Thesis, University of Pittsburgh.
(Unpublished)
Abstract
The mechanism for the iron-catalyzed C–H functionalization of simple monosubstituted allenes is investigated. In this report, we determined that the mechanism of this transformation involves a deprotonation causing the organoiron species to transform from a datively bound η2-allene complex to a neutral η1-propargyliron complex. This iron species acts as a nucleophile for in-situ generated electrophiles, performing a SE2’ type reaction resulting in a disubstituted allene. Herein, we additionally discuss the subtle differences in ligand design and the ramifications on various reaction yields through analysis of electronic properties and x-ray structure.
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| Item Type: |
University of Pittsburgh ETD
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| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
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| Date: |
10 May 2023 |
| Date Type: |
Publication |
| Defense Date: |
30 March 2023 |
| Approval Date: |
10 May 2023 |
| Submission Date: |
16 March 2023 |
| Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
| Number of Pages: |
55 |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
MS - Master of Science |
| Thesis Type: |
Master's Thesis |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
Iron Catalysis
Allene Transformation
Iron Cyclopentadiene
Piano stool complex |
| Date Deposited: |
10 May 2023 18:57 |
| Last Modified: |
10 Apr 2025 19:31 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/44383 |
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