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Radical Benzylation of Quinones via C–H Abstraction
preprintsubmitted on 05.04.2019, 15:47 and posted on 08.04.2019, 15:03 by Jordan D. Galloway, Duy N. Mai, Ryan Baxter
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 ben-zylic carbons. The use of pre-formed Ag(4–OMePy)2NO3 as a catalyst proved effective in improving reaction efficiency by reducing unwanted degradation pathways available to Selectfluor.
Read the published paper
in The Journal of Organic Chemistry
CAREER: Mechanistic Study of Radical Initiations for Aromatic Functionalization
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