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Issue 9, 2019
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Catalytic β C–H amination via an imidate radical relay

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Abstract

The first catalytic strategy to harness imidate radicals for C–H functionalization has been developed. This iodine-catalyzed approach enables β C–H amination of alcohols by an imidate-mediated radical relay. In contrast to our first-generation, (super)stoichiometric protocol, this catalytic method enables faster and more efficient reactivity. Furthermore, lower oxidant concentration affords broader functional group tolerance, including alkenes, alkynes, alcohols, carbonyls, and heteroarenes. Mechanistic experiments interrogating the electronic nature of the key 1,5 H-atom transfer event are included, as well as probes for chemo-, regio-, and stereo-selectivity.

Graphical abstract: Catalytic β C–H amination via an imidate radical relay

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Publication details

The article was received on 20 Dec 2018, accepted on 09 Jan 2019 and first published on 17 Jan 2019


Article type: Edge Article
DOI: 10.1039/C8SC05685D
Chem. Sci., 2019,10, 2693-2699
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Catalytic β C–H amination via an imidate radical relay

    L. M. Stateman, E. A. Wappes, K. M. Nakafuku, K. M. Edwards and D. A. Nagib, Chem. Sci., 2019, 10, 2693
    DOI: 10.1039/C8SC05685D

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