Quinone C–H Alkylations via Oxidative Radical Processes

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 persu...

Full description

Saved in:
Bibliographic Details
Published in:Synthesis (Stuttgart) 2018-08, Vol.50 (15), p.2915-2923
Main Authors: Hamsath, Akil, Galloway, Jordan D., Baxter, Ryan D.
Format: Article
Language:English
Subjects:
special topic
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0037-1610005