Radical Benzylation of Quinones via C-H Abstraction.
- Author(s): Galloway, Jordan D;
- Mai, Duy N;
- Baxter, Ryan D
- et al.
Published Web Locationhttps://doi.org/10.1021/acs.joc.9b01004
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.