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Radical Benzylation of Quinones via C–H Abstraction

preprint
submitted on 05.04.2019 and posted on 08.04.2019 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.

Funding

CAREER: Mechanistic Study of Radical Initiations for Aromatic Functionalization

Directorate for Mathematical & Physical Sciences

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History

Email Address of Submitting Author

rbaxter@ucmerced.edu

Institution

University of California, Merced

Country

United States

ORCID For Submitting Author

0000-0002-1341-5315

Declaration of Conflict of Interest

No conflict of interest

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in The Journal of Organic Chemistry

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