In Situ Reduction and Functionalization of Polycyclic Quinones

Karl J. Thorley, Yang Song, Sean R. Parkin, John E. Anthony

Research output: Contribution to journalArticlepeer-review


Attempts to functionalize polycyclic quinones using lithium diisopropylamide as a base led to the unexpected formation of acenes. This reaction proceeds by electron transfer from the base to the electron deficient quinone, whose radical anion can react with a variety of electrophiles. Siloxy derivatives synthesized by this method could be easily isolated but showed poor photostability. In situ reduced intermediate generation is a convenient approach to functionalization of oxidatively unstable hydroquinones.

Original languageEnglish
Pages (from-to)7193-7196
Number of pages4
JournalOrganic Letters
Issue number18
StatePublished - Sep 18 2020

Bibliographical note

Funding Information:
Support for this work was provided by the U.S. Department of Energy, Office of Basic Energy Sciences (ERW7404), and the MRI program of the National Science Foundation (Grants CHE-0319176 and CHE-1625732).

Publisher Copyright:
© 2020 American Chemical Society.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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