4.8 Article

Catalytic β C-H amination via an imidate radical relay

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CHEMICAL SCIENCE
卷 10, 期 9, 页码 2693-2699

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc05685d

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资金

  1. National Institutes of Health [NIH R35 GM119812]
  2. National Science Foundation [NSF CAREER 1654656]
  3. NSF GRFP Fellowship

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The first catalytic strategy to harness imidate radicals for C-H functionalization has been developed. This iodine-catalyzed approach enables beta 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.

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