Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C–H activation

Huang, Xiongyi; Groves, John T.

doi:10.1007/s00775-016-1414-3

Title: Beyond ferryl-mediated hydroxylation: 40 years of the rebound mechanism and C–H activation

Journal Article · Thu Dec 01 04:00:00 UTC 2016 · JBIC Journal of Biological Inorganic Chemistry

DOI: https://doi.org/10.1007/s00775-016-1414-3 · OSTI ID:1397173

Huang, Xiongyi ^[1]; Groves, John T. ^[1]

Princeton Univ., NJ (United States)

Since our initial report in 1976, the oxygen rebound mechanism has become the consensus mechanistic feature for an expanding variety of enzymatic C–H functionalization reactions and small molecule biomimetic catalysts. For both the biotransformations and models, an initial hydrogen atom abstraction from the substrate (R–H) by high-valent iron-oxo species (Feⁿ=O) generates a substrate radical and a reduced iron hydroxide, [Fe^n-1–OH ·R]. This caged radical pair then evolves on a complicated energy landscape through a number of reaction pathways, such as oxygen rebound to form R–OH, rebound to a non-oxygen atom affording R–X, electron transfer of the incipient radical to yield a carbocation, R⁺, desaturation to form olefins, and radical cage escape. These various flavors of the rebound process, often in competition with each other, give rise to the wide range of C–H functionalization reactions performed by iron-containing oxygenases. In this review, we first recount the history of radical rebound mechanisms, their general features, and key intermediates involved. We will discuss in detail the factors that affect the behavior of the initial caged radical pair and the lifetimes of the incipient substrate radicals. Several representative examples of enzymatic C–H transformations are selected to illustrate how the behaviors of the radical pair [Fe^n-1–OH ·R] determine the eventual reaction outcome. Finally, we discuss the powerful potential of “radical rebound” processes as a general paradigm for developing novel C–H functionalization reactions with synthetic, biomimetic catalysts. We envision that new chemistry will continue to arise by bridging enzymatic “radical rebound” with synthetic organic chemistry.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Center for Catalytic Hydrocarbon Functionalization (CCHF)

Sponsoring Organization:: USDOE SC Office of Basic Energy Sciences (SC-22)

Grant/Contract Number:: SC0001298

OSTI ID:: 1397173

Journal Information:: JBIC Journal of Biological Inorganic Chemistry, Journal Name: JBIC Journal of Biological Inorganic Chemistry Journal Issue: 2-3 Vol. 22; ISSN 0949-8257

Publisher:: SpringerCopyright Statement

Country of Publication:: United States

Language:: English

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In Vitro Reconstitution of OxyC Activity Enables Total Chemoenzymatic Syntheses of Vancomycin Aglycone Variants Forneris, Clarissa C.; Seyedsayamdost, Mohammad R. Angewandte Chemie, Vol. 130, Issue 27 https://doi.org/10.1002/ange.201802856	journal	July 2018
cPCET versus HAT: A Direct Theoretical Method for Distinguishing X-H Bond-Activation Mechanisms Klein, Johannes E. M. N.; Knizia, Gerald Angewandte Chemie, Vol. 130, Issue 37 https://doi.org/10.1002/ange.201805511	journal	August 2018
Site- and Enantioselective C−H Oxygenation Catalyzed by a Chiral Manganese Porphyrin Complex with a Remote Binding Site Burg, Finn; Gicquel, Maxime; Breitenlechner, Stefan Angewandte Chemie International Edition, Vol. 57, Issue 11 https://doi.org/10.1002/anie.201712340	journal	February 2018
In Vitro Reconstitution of OxyC Activity Enables Total Chemoenzymatic Syntheses of Vancomycin Aglycone Variants Forneris, Clarissa C.; Seyedsayamdost, Mohammad R. Angewandte Chemie International Edition, Vol. 57, Issue 27 https://doi.org/10.1002/anie.201802856	journal	July 2018
cPCET versus HAT: A Direct Theoretical Method for Distinguishing X-H Bond-Activation Mechanisms Klein, Johannes E. M. N.; Knizia, Gerald Angewandte Chemie International Edition, Vol. 57, Issue 37 https://doi.org/10.1002/anie.201805511	journal	August 2018
Mechanism of Oxidative Activation of Fluorinated Aromatic Compounds by N‐Bridged Diiron‐Phthalocyanine: What Determines the Reactivity? Colomban, Cédric; Tobing, Anthonio H.; Mukherjee, Gourab Chemistry – A European Journal, Vol. 25, Issue 63 https://doi.org/10.1002/chem.201902934	journal	September 2019
Design of A Metabolically Stable Tritium-Tracer of the PI3K δ -Inhibitor CDZ173 (Leniolisib) as a Tool to Study Liver Metabolites Bauer, Carsten; Luu, Tong; Eggimann, Fabian Helvetica Chimica Acta, Vol. 101, Issue 6 https://doi.org/10.1002/hlca.201800044	journal	June 2018
Cu‐Mediated C7 Acetoxylation of Indolines Gao, Shanshan; Xu, Xing; Tang, Hao ChemistrySelect, Vol. 4, Issue 19 https://doi.org/10.1002/slct.201901170	journal	May 2019
Manganese-salen catalyzed oxidative benzylic chlorination Sasmal, Sheuli; Rana, Sujoy; Lahiri, Goutam Kumar Journal of Chemical Sciences, Vol. 130, Issue 7 https://doi.org/10.1007/s12039-018-1511-7	journal	July 2018
Iron-based trinuclear metal-organic nanostructures on a surface with local charge accumulation Krull, Cornelius; Castelli, Marina; Hapala, Prokop Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-05543-4	journal	August 2018
Recent examples of α-ketoglutarate-dependent mononuclear non-haem iron enzymes in natural product biosyntheses Gao, Shu-Shan; Naowarojna, Nathchar; Cheng, Ronghai Natural Product Reports, Vol. 35, Issue 8 https://doi.org/10.1039/c7np00067g	journal	January 2018
Enantioselective aliphatic C–H bond oxidation catalyzed by bioinspired complexes Milan, Michela; Bietti, Massimo; Costas, Miquel Chemical Communications, Vol. 54, Issue 69 https://doi.org/10.1039/c8cc03165g	journal	January 2018
Cercosporin-bioinspired selective photooxidation reactions under mild conditions Li, Jia; Bao, Wenhao; Tang, Zhaocheng Green Chemistry, Vol. 21, Issue 22 https://doi.org/10.1039/c9gc02270h	journal	January 2019
Visible-light photocatalytic aerobic oxidation of sulfides to sulfoxides with a perylene diimide photocatalyst Gao, Yueying; Xu, Huan; Zhang, Shiwei Organic & Biomolecular Chemistry, Vol. 17, Issue 30 https://doi.org/10.1039/c9ob00945k	journal	January 2019
Enantioselective oxygenation of exocyclic methylene groups by a manganese porphyrin catalyst with a chiral recognition site Burg, Finn; Breitenlechner, Stefan; Jandl, Christian Chemical Science, Vol. 11, Issue 8 https://doi.org/10.1039/c9sc06089h	journal	January 2020
Enhancing microperoxidase activity and selectivity: immobilization in metal-organic frameworks Gkaniatsou, Effrosyni; Serre, Christian; Mahy, Jean-Pierre Porphyrin Science by Women https://doi.org/10.1142/9789811223556_0101	book	January 2021
Enhancing microperoxidase activity and selectivity: immobilization in metal-organic frameworks Gkaniatsou, Effrosyni; Serre, Christian; Mahy, Jean-Pierre Journal of Porphyrins and Phthalocyanines, Vol. 23, Issue 07n08 https://doi.org/10.1142/s1088424619300106	journal	July 2019
Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis Verschueren, Rik H.; De Borggraeve, Wim M. Molecules, Vol. 24, Issue 11 https://doi.org/10.3390/molecules24112122	journal	June 2019
Iron-based trinuclear metal-organic nanostructures on a surface with local charge accumulation Krull, Cornelius; Castelli, Marina; Hapala, Prokop arXiv https://doi.org/10.48550/arxiv.1802.09146	text	January 2018

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