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Investigation of transition metal-catalyzed nitrene transfer reactions in water
Juliet M Alderson1, Joshua R Corbin1, Jennifer M Schomaker1
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706 USA.
Abstract:
Transition metal-catalyzed nitrene transfer is a powerful method for incorporating new CN bonds into relatively unfunctionalized scaffolds. In this communication, we report the first examples of site- and chemoselective CH bond amination reactions in aqueous media. The unexpected ability to employ water as the solvent in these reactions is advantageous in that it eliminates toxic solvent use and enables reactions to be run at increased concentrations with lower oxidant loadings. Using water as the reaction medium has potential to expand the scope of nitrene transfer to encompass a variety of biomolecules and highly polar substrates, as well as enable pH control over the site-selectivity of CH bond amination.
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