Site-Selective Copper-Catalyzed Azidation of Benzylic C–H Bonds
Top Cited Papers
- 23 June 2020
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 142 (26), 11388-11393
- https://doi.org/10.1021/jacs.0c05362
Abstract
Site selectivity represents a key challenge for non-directed C–H functionalization, even when the C–H bond is intrinsically reactive. Here, we report a copper-catalyzed method for benzylic C–H azidation of diverse molecules. Experimental and density functional theory studies suggest the benzyl radical reacts with a CuII-azide species via a radical-polar crossover pathway. Comparison of this method with other C–H azidation methods highlights its unique site selectivity, and conversions of the benzyl azide products into amine, triazole, tetrazole, and pyrrole functional groups highlight the broad utility of this method for target molecule synthesis and medicinal chemistry.Keywords
Funding Information
- University of Minnesota
- National Institute of General Medical Sciences (R01 GM126832, R35 GM134929)
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