Samantha M. Brewer
Mechanistic Insights into Iron-Catalyzed C-H Bond Activation and C-C Coupling
Brewer, Samantha M.; Schwartz, Timothy M.; Mekhail, Magy A.; Turan, Lara S.; Prior, Timothy J.; Hubin, Timothy J.; Janesko, Benjamin G.; Green, Kayla N.
Authors
Timothy M. Schwartz
Magy A. Mekhail
Lara S. Turan
Dr Tim Prior T.Prior@hull.ac.uk
Senior Lecturer in Inorganic Chemistry
Timothy J. Hubin
Benjamin G. Janesko
Kayla N. Green
Abstract
Iron-catalyzed C-C coupling reactions of pyrrole provide a unique alternative to the traditional Pd-catalyzed counterpart. However, many details regarding the actual mechanism remain unknown. A series of macrocyclic iron(III) complexes were used to evaluate specifics related to the role of O2, radicals, and μ-oxodiiron-complex participation in the catalytic cycle. It was determined that the mononuclear tetra-azamacrocyclic complex is a true catalyst and not a stoichiometric reagent, while more than one equivalent of a sacrificial oxidant is needed. Furthermore, the reaction does not proceed through an organic radical pathway. μ-Oxodiiron complexes are not involved in the main catalytic pathway, and the dimers are, in fact, off-cycle species that decrease catalytic efficiency.
Citation
Brewer, S. M., Schwartz, T. M., Mekhail, M. A., Turan, L. S., Prior, T. J., Hubin, T. J., …Green, K. N. (in press). Mechanistic Insights into Iron-Catalyzed C-H Bond Activation and C-C Coupling. Organometallics, https://doi.org/10.1021/acs.organomet.1c00211
Journal Article Type | Article |
---|---|
Acceptance Date | Jul 2, 2021 |
Online Publication Date | Jul 20, 2021 |
Deposit Date | Jul 22, 2021 |
Publicly Available Date | Jul 21, 2022 |
Journal | Organometallics |
Print ISSN | 0276-7333 |
Electronic ISSN | 1520-6041 |
Publisher | American Chemical Society |
Peer Reviewed | Peer Reviewed |
DOI | https://doi.org/10.1021/acs.organomet.1c00211 |
Keywords | Absorption; Ligands; Oligomers; Pyrroles; Oxygen |
Public URL | https://hull-repository.worktribe.com/output/3808910 |
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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organometallics, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.organomet.1c00211