ArticleNature chemistry2011
Diverting non-haem iron catalysed aliphatic C-H hydroxylations towards desaturations.
Article in Nature chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 44 papers.
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Who cites it
44 citing papers in PubMed.
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- Flash Communication: Flexibility of a Biologically Inspired Ligand Framework for Intramolecular C-H Activation.Organometallics · 2025Article
- Iron-Catalyzed Aerobic Carbonylation of Methane via Ligand-to-Metal Charge Transfer Excitation.Journal of the American Chemical Society · 2025Article
- Intramolecular C-H Oxidation in Iron(V)-oxo-carboxylato Species Relevant in the γ-Lactonization of Alkyl Carboxylic Acids.ACS catalysis · 2024Article
- Dehydrogenative synthesis ofScience advances · 2024Article
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- A preparative small-molecule mimic of liver CYP450 enzymes in the aliphatic C-H oxidation of carbocyclicProceedings of the National Academy of Sciences of the United States of America · 2023Article
- Multiple remote C(spChemical science · 2022Article
- One-pot chlorocarboxylation of toluenes with chlorine dioxide under photoirradiation.RSC advances · 2022Article
- γ C-H Functionalization of Amines via Triple H-Atom Transfer of a Vinyl Sulfonyl Radical Chaperone.Journal of the American Chemical Society · 2022Article
- Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light.Chemical science · 2022Article
- Resolving Oxygenation Pathways in Manganese-Catalyzed C(spJournal of the American Chemical Society · 2022Article
- Ruthenium-Catalyzed Dehydrogenation Through an Intermolecular Hydrogen Atom Transfer Mechanism.Angewandte Chemie (International ed. in English) · 2021Article
- Desaturation via Redox-Neutral Hydrogen Transfer Process: Synthesis of 2-Allyl Anilines, Mechanism and Applications.iScience · 2020Article
- Copper-catalyzed dehydrogenative γ-C(spNature communications · 2019Article
- Development of a Terpene Feedstock-Based Oxidative Synthetic Approach to the Illicium Sesquiterpenes.Journal of the American Chemical Society · 2019Article
- Aliphatic C-H Oxidations for Late-Stage Functionalization.Journal of the American Chemical Society · 2018Review
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3 authors.
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Abstract
Carboxylate-ligated, non-haem iron enzymes demonstrate the capacity for catalysing such remarkable processes as hydroxylations, chlorinations and desaturations of inert, aliphatic C-H bonds. A key to functional diversity is the enzymes' ability to divert fleeting radicals towards different types of functionalization using active site and/or substrate modifications. We report that a non-haem iron hydroxylase catalyst [Fe(PDP)] can also be diverted to catalytic, mixed hydroxylase/desaturase activity with aliphatic C-H bonds. Using a taxane-based radical trap that rearranges under Fe(PDP) oxidation to furnish a nortaxane skeleton, we provide the first direct evidence for a substrate radical using this class of stereoretentive hydroxylation catalysts. Hydroxylation and desaturation proceed by means of a short-lived radical that diverges in a substrate-dependent manner in the presence of carboxylic acids. The novel biomimetic reactivity displayed by this small molecule catalyst is harnessed to diversify natural product derivatives as well as interrogate their biosynthetic pathways.
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