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Mechanistic Insights into Iron-Catalyzed Allenic C⁠–H Functionalization

Palermo, Philip (2023) Mechanistic Insights into Iron-Catalyzed Allenic C⁠–H Functionalization. Master's Thesis, University of Pittsburgh. (Unpublished)

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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
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Palermo, Philippnp13@pitt.edupnp130009-0002-7309-694X
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Thesis AdvisorWang,
Committee ChairTransue, Wesleywtransue@pitt.eduwtransue
Committee ChairBrummond, Kaykbrummon@pitt.edukbrummon
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 May 2023 18:57

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  • Mechanistic Insights into Iron-Catalyzed Allenic C⁠–H Functionalization. (deposited 10 May 2023 18:57) [Currently Displayed]


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