Synfacts 2018; 14(02): 0195
DOI: 10.1055/s-0037-1609142
DOI: 10.1055/s-0037-1609142
Organo- and Biocatalysis
Organocatalytic C(sp3)–H Amination through Nitrenoid Transfer
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: DOI: 10.1039/C7SC03968A.
Organocatalytic Nitrenoid Transfer: Metal-Free Selective Intermolecular C(sp3)–H Amination Catalyzed by an Iminium Salt.
Chem. Sci. 2018;
DOI: DOI: 10.1039/C7SC03968A.
Further Information
Publication History
Publication Date:
18 January 2018 (online)
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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