Synthesis 2018; 50(15): 2915-2923
DOI: 10.1055/s-0037-1610005
special topic
© Georg Thieme Verlag Stuttgart · New York

Quinone C–H Alkylations via Oxidative Radical Processes

Akil Hamsath
Department of Chemistry & Chemical Biology, University of California, Merced, 5200 N. Lake Road, Merced, CA 95343, USA   Email: rbaxter@ucmerced.edu
,
Jordan D. Galloway
Department of Chemistry & Chemical Biology, University of California, Merced, 5200 N. Lake Road, Merced, CA 95343, USA   Email: rbaxter@ucmerced.edu
,
Department of Chemistry & Chemical Biology, University of California, Merced, 5200 N. Lake Road, Merced, CA 95343, USA   Email: rbaxter@ucmerced.edu
› Author Affiliations
We gratefully acknowledge the University of California, Merced for funding. R.D.B acknowledges funding from the University of California, Merced MACES Center, NASA parent.
Further Information

Publication History

Received: 01 March 2018

Accepted after revision: 18 April 2018

Publication Date:
06 June 2018 (eFirst)

Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

A brief survey of radical additions to quinones is reported. Carboxylic acids, aldehydes, and unprotected amino acids are compared as alkyl radical precursors for the mono- or bis- C–H alkylation of several quinones. Two methods for radical initiation are discussed comparing inorganic persulfates and Selectfluor as stoichiometric oxidants. Kinetic analysis reveals dramatic differences in the rate of radical initiation depending on the identity of the radical precursor and oxidant. Synthetic strategies for efficiently producing alkyl-quinones are discussed in the context of selecting optimum radical precursors and initiators depending on quinone identity and functional groups present.

Supporting Information

 
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