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Synthesis 2018; 50(15): 2915-2923
DOI: 10.1055/s-0037-1610005
DOI: 10.1055/s-0037-1610005
special topic
Quinone C–H Alkylations via Oxidative Radical Processes
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 (online)
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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610005.
- Supporting Information
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