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Open Access Publications from the University of California

Radical Benzylation of Quinones via C-H Abstraction.

  • Author(s): Galloway, Jordan D
  • Mai, Duy N
  • Baxter, Ryan D
  • et al.

Herein we report the development of radical benzylation reactions of quinones using Selectfluor and catalytic Ag(I) initiators. The reaction is believed to proceed via a C-H abstraction mechanism after Ag(I)-mediated reduction of Selectfluor. This reaction occurs under mild conditions and is effective for a variety of quinones and radical precursors bearing primary benzylic carbons. The use of preformed Ag(4-OMePy)2NO3 as a catalyst proved effective in improving the reaction efficiency by reducing unwanted degradation pathways available to Selectfluor.

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