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Synfacts 2018; 14(02): 0195
DOI: 10.1055/s-0037-1609142
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic C(sp3)–H Amination through Nitrenoid Transfer

Contributor(s):
Benjamin List
,
Nobuya Tsuji
Combee LA. Raya B. Wang D. Hilinski MK. * University of Virginia, Charlottesville, USA
Organocatalytic Nitrenoid Transfer: Metal-Free Selective Intermolecular C(sp3)–H Amination Catalyzed by an Iminium Salt.

Chem. Sci. 2018;
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Further Information

Publication History

Publication Date:
18 January 2018 (online)

 
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Key words

nitrenoid transfer - amination - iminium salt

Significance

The Hilinski group reports a C(sp3)–H amination through a nitrenoid transfer catalyzed by iminium salt A. The reaction proceeds in moderate to high yields, and the method is applicable to several natural products having other functional groups.


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Comment

In contrast to reported nitrenoid-transfer reactions catalyzed by transition metals, the authors developed an organocatalytic variant of the transformation. They proposed the di­aziridinium salt as critical intermediate, which is supported by ESI-MS analysis, but not yet fully characterized. A kinetic isotopic effect study suggested C–H cleavage as the rate-determining step.


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