ArticleOrganic letters2016
Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C-H Sites.
Article in Organic letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- An alkyl-swap platform for late-stage modification of secondary N-methylamines.Nature chemistry · 2026Article
- Selective C-H Activation of Unprotected Allylamines by Control of Catalyst Speciation.Chem catalysis · 2023Article
- Chemoselective Oxyfunctionalization of Functionalized Benzylic Compounds with a Manganese Catalyst.Angewandte Chemie (International ed. in English) · 2022Article
- Amine Organocatalysis of Remote, Chemoselective C(spACS catalysis · 2022Article
- Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.Chemical reviews · 2022Review
- Palladium-Mediated CAngewandte Chemie (International ed. in English) · 2021Article
- An efficient and practical aerobic oxidation of benzylic methylenes by recyclableRSC advances · 2021Article
- C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods.SynOpen (2017) · 2021Article
- Article
- Bio-inspired iron-catalyzed oxidation of alkylarenes enables late-stage oxidation of complex methylarenes to arylaldehydes.Nature communications · 2019Article
- Primary α-tertiary amine synthesisChemical science · 2019Article
- Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.Journal of the American Chemical Society · 2018Article
- Selective Heteroaryl N-Oxidation of Amine-Containing Molecules.Organic letters · 2018Article
- A general method for the metal-free, regioselective, remote C-H halogenation of 8-substituted quinolines.Chemical science · 2018Article
- Chemoselective Aliphatic C-H Bond Oxidation Enabled by Polarity Reversal.ACS central science · 2017Article
- Remote C(spOrganic letters · 2017Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
We report the development of an iron-catalyzed method for the selective oxyfunctionalization of benzylic C(sp(3))-H bonds in aliphatic amine substrates. This transformation is selective for benzylic C-H bonds that are remote (i.e., at least three carbons) from the amine functional group. High site selectivity is achieved by in situ protonation of the amine with trifluoroacetic acid, which deactivates more traditionally reactive C-H sites that are α to nitrogen. The scope and synthetic utility of this method are demonstrated via the synthesis and derivatization of a variety of amine-containing, biologically active molecules.
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