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Computational Studies of Metal Free C−H Bond Functionalization

Morales Rivera, Cristian A. (2020) Computational Studies of Metal Free C−H Bond Functionalization. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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Carbon–hydrogen bond functionalization reactions can greatly facilitate chemical synthesis due to their capability to increase molecular complexity from readily available starting materials with minimal waste generation. These processes are most often achieved through transition metal catalysis, though metal-free approaches for such reactions are becoming increasingly common. DDQ and hypervalent iodine reagents have shown to be greatly useful for promoting C–H cleavage. DFT calculations presented in this dissertation were performed to study the mechanistic pathways of metal free C–H functionalization mediated by DDQ and various hypervalent iodine reagents. These computational investigations not only replicate and explain the experimental observations, but also provide a better understanding of the reaction mechanisms and factors contributing to the reactivity and selectivity. These computational insights were used to develop a predictive reactivity model for the DDQ-mediated C–H functionalization.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Morales Rivera, Cristian A.cam2982pitt.educam298
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairLiu, Peng
Committee MemberMpourmpakis, Giannis
Committee MemberLambrecht, Daniel S.
Committee MemberFloreancig, Paul
Date: 16 January 2020
Date Type: Publication
Defense Date: 28 August 2019
Approval Date: 16 January 2020
Submission Date: 2 October 2019
Access Restriction: 1 year -- Restrict access to University of Pittsburgh for a period of 1 year.
Number of Pages: 148
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: DFT, metal free, C-H bond functionalization, hypervalent iodine, DDQ
Date Deposited: 16 Jan 2020 19:16
Last Modified: 16 Jan 2021 06:15


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