ArticleACS central science2017
Chemoselective Aliphatic C-H Bond Oxidation Enabled by Polarity Reversal.
Article in ACS central science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 36 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
36 citing papers in PubMed.
- Solvophobic Effect-Driven C4-Selective C-H Oxidation of Diverse Alkyl Substrates by a Macrocyclic Supramolecular Catalyst.Journal of the American Chemical Society · 2026Article
- Article
- Installing Axial Chirality by Atroposelective C(spJournal of the American Chemical Society · 2026Article
- Convergent Synthesis of Tetradentate Aminopyridine C-H Oxidation Catalysts.ACS organic & inorganic Au · 2026Article
- Desymmetrization of Malonic Monoesters and Malonic Acids via Enantioselective Catalytic C(spAngewandte Chemie (International ed. in English) · 2026Article
- Fluorinated Solvents for Chemoselective Oxidations: A Strategy toward Synthetic Ideality in Natural Product Synthesis.ACS organic & inorganic Au · 2026Article
- Asymmetric Hydrogen Atom Transfer.ACS catalysis · 2026Review
- Article
- Immunomodulation and Mechanical Characterization of Manuka Honey-Incorporated Near-Field Electrospun Bioresorbable Vascular Grafts.Bioengineering (Basel, Switzerland) · 2025Article
- Cationic, Iodine(III)-Mediated and Directed Diastereoselective Oxidation of Inert C-H Bonds in Cyclic Hydrocarbons.Angewandte Chemie (International ed. in English) · 2025Article
- Biosynthesis of the Antifungal Polyhydroxy-Polyketide Acrophialocinol.Organic letters · 2025Article
- Concise and Free-Metal Access to Lactone-Annelated Pyrrolo[2,1-International journal of molecular sciences · 2024Article
- Radical and Cationic Pathways in C(Journal of the American Chemical Society · 2023Article
- Highly Selective C(spJournal of the American Chemical Society · 2023Article
- Recent Advances in C-H Functionalisation through Indirect Hydrogen Atom Transfer.Molecules (Basel, Switzerland) · 2023Review
- C-H Bonds as Functional Groups: Simultaneous Generation of Multiple Stereocenters by Enantioselective Hydroxylation at Unactivated Tertiary C-H Bonds.Journal of the American Chemical Society · 2023Article
- 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
- Peracid Oxidation of Unactivated spChemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Anaerobic Hydroxylation of C(spJournal of the American Chemical Society · 2023Article
- Selective Oxidation of Alcohols through FeChemistryOpen · 2022Article
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Methods for selective oxidation of aliphatic C-H bonds are called on to revolutionize organic synthesis by providing novel and more efficient paths. Realization of this goal requires the discovery of mechanisms that can alter in a predictable manner the innate reactivity of these bonds. Ideally, these mechanisms need to make oxidation of aliphatic C-H bonds, which are recognized as relatively inert, compatible with the presence of electron rich functional groups that are highly susceptible to oxidation. Furthermore, predictable modification of the relative reactivity of different C-H bonds within a molecule would enable rapid diversification of the resulting oxidation products. Herein we show that by engaging in hydrogen bonding, fluorinated alcohols exert a polarity reversal on electron rich functional groups, directing iron and manganese catalyzed oxidation toward a priori stronger and unactivated C-H bonds. As a result, selective hydroxylation of methylenic sites in hydrocarbons and remote aliphatic C-H oxidation of otherwise sensitive alcohol, ether, amide, and amine substrates is achieved employing aqueous hydrogen peroxide as oxidant. Oxidations occur in a predictable manner, with outstanding levels of product chemoselectivity, preserving the first-formed hydroxylation product, thus representing an extremely valuable tool for synthetic planning and development.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.