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

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;
DOI: 10.1039/C7SC03968A.
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18. Januar 2018 (online)



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.



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.