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Iron-Catalyzed C–H Functionalization of Alkenes for Addition to Conjugated Electrophiles

Scrivener, Sarah (2024) Iron-Catalyzed C–H Functionalization of Alkenes for Addition to Conjugated Electrophiles. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Abstract

Allylic C(sp3)–H functionalization of simple alkenes, and subsequent coupling with Michael acceptors in a base metal catalyzed process offers a practical and modular approach to a variety of scaffolds. In this dissertation, the redox-neutral deprotonative generation of catalytic allyliron intermediates using a pentamethylcyclopentadienyliron(II) dicarbonyl catalyst provides an allyl anion equivalent for addition into α,β-unsaturated carbonyl derivatives. A wide range of alkene substrates serve as allyl pronucleophiles and undergo 1,4-conjugate addition to chalcone type electrophiles and other enones. Furthermore, Michael addition of alkenes to a collection of cyclic and acyclic nitrogen-containing compounds featuring C–C unsaturation, such as maleimides and enaminones, is also described. For some sterically hindered electrophiles, an alternative linear regioselectivity was observed. A preliminary investigation into the formation of these unexpected products is discussed.

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Details

Item Type: University of Pittsburgh ETD
Status: Unpublished
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Scrivener, Sarahsgs49@pitt.eduSGS49
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWang, Yi-MingYIMINGW@pitt.edu
Committee MemberBrummond, Kaykbrummon@pitt.edu
Committee MemberKoide, Kazunorikoide@pitt.edu
Committee MemberKristina, Pazehoskipazehoskiko@gcc.edu
Date: 13 May 2024
Date Type: Publication
Defense Date: 28 March 2024
Approval Date: 13 May 2024
Submission Date: 7 March 2024
Access Restriction: 2 year -- Restrict access to University of Pittsburgh for a period of 2 years.
Number of Pages: 503
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, Michael Addition, Iron
Date Deposited: 13 May 2024 13:56
Last Modified: 13 May 2024 13:56
URI: http://d-scholarship.pitt.edu/id/eprint/45848

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