Morales Rivera, Cristian A.
(2020)
Computational Studies of Metal Free C−H Bond Functionalization.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
Abstract
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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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
| Creators | Email | Pitt Username | ORCID  |
|---|
| Morales Rivera, Cristian A. | cam2982pitt.edu | cam298 | |
|
| ETD Committee: |
| Title | Member | Email Address | Pitt Username | ORCID |
|---|
| Committee Chair | Liu, Peng | | | | | Committee Member | Mpourmpakis, Giannis | | | | | Committee Member | Lambrecht, Daniel S. | | | | | Committee Member | Floreancig, 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 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/37689 |
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