Issue 9, 2019

Catalytic β C–H amination via an imidate radical relay


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

Supplementary files

Article information

Article type
Edge Article
20 Dec 2018
09 Jan 2019
First published
17 Jan 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 2693-2699

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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