Site-Selective Copper-Catalyzed Azidation of Benzylic C-H Bonds

Sung Eun Suh, Si Jie Chen, Mukunda Mandal, Ilia A. Guzei, Christopher J. Cramer, Shannon S. Stahl

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)11388-11393
Number of pages6
JournalJournal of the American Chemical Society
Volume142
Issue number26
DOIs
StatePublished - Jul 1 2020

PubMed: MeSH publication types

  • Journal Article
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, N.I.H., Extramural

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