ArticleJournal of the American Chemical Society2017
Site-Selective Copper-Catalyzed Amination and Azidation of Arenes and Heteroarenes via Deprotonative Zincation.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- ZnFeChemistryOpen · 2026Article
- Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.Chemical reviews · 2024Review
- Synthesis of Oligonucleotides Carrying Inter-nucleotideACS omega · 2023Article
- Selective desaturation of amides: a direct approach to enamides.Chemical science · 2022Article
- General stereoretentive preparation of chiral secondary mixed alkylmagnesium reagents and their use for enantioselective electrophilic aminations.Chemical science · 2021Article
- Ligand-free copper-catalyzed C(spRSC advances · 2021Article
- Iron-Mediated Electrophilic Amination of Organozinc Halides using Organic Azides.Angewandte Chemie (International ed. in English) · 2020Article
- Methods for direct C(spRSC advances · 2019Review
- Cross-Coupling of Heteroatomic Electrophiles.Chemical reviews · 2019Review
- Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades.Angewandte Chemie (International ed. in English) · 2019Article
- A new route for the efficient metalation of unfunctionalized aromatics.Chemical science · 2019Article
- Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines.Journal of the American Chemical Society · 2019Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Arene amination is achieved by site-selective C-H zincation followed by copper-catalyzed coupling with O-benzoylhydroxylamines under mild conditions. Key to this success is ortho-zincation mediated by lithium amidodiethylzincate base that is effective for a wide range of arenes, including nonactivated arenes bearing simple functionalities such as fluoride, chloride, ester, amide, ether, nitrile, and trifluoromethyl groups as well as heteroarenes including indole, thiophene, pyridine, and isoquinoline. An analogous C-H azidation is also accomplished using azidoiodinane for direct introduction of a useful azide group onto a broad scope of arenes and heteroarenes. These new transformations offer rapid access to valuable and diverse chemical space of aminoarenes. Their broad applications in organic synthesis and drug discovery are demonstrated in the synthesis of novel analogues of natural product (-)-nicotine and antidepressant sertraline by late-stage amination and azidation reactions.
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