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Issue 4, 2018
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Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp3)–H amination catalyzed by an iminium salt

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Abstract

This report details the first organocatalytic method for nitrenoid transfer and its application to intermolecular, site-selective C(sp3)–H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87%. A mechanistic proposal for the observed reactivity supported by experimental evidence invokes the intermediacy of a diaziridinium salt or related organic nitrenoid, species that have not been previously explored for the purpose of C–H amination. Finally, examples of late-stage functionalization of complex molecules highlight the selectivity and potential utility of this catalytic method in synthesis.

Graphical abstract: Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp3)–H amination catalyzed by an iminium salt

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Supplementary files

Article information


Submitted
10 Sep 2017
Accepted
26 Nov 2017
First published
27 Nov 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 935-939
Article type
Edge Article

Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp3)–H amination catalyzed by an iminium salt

L. A. Combee, B. Raya, D. Wang and M. K. Hilinski, Chem. Sci., 2018, 9, 935
DOI: 10.1039/C7SC03968A

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