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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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Supplementary files

Article information


Submitted
20 Dec 2018
Accepted
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

Chem. Sci., 2019,10, 2693-2699
Article type
Edge Article

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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