期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 142, 期 26, 页码 11388-11393出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c05362
关键词
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资金
- NIH [R01 GM126832, R35 GM134929]
- University of Minnesota
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 Cu-II-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.
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