In Situ Reduction and Functionalization of Polycyclic Quinones

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

doi:10.1021/acs.orglett.0c02529

In Situ Reduction and Functionalization of Polycyclic Quinones

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

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

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 language	English
Pages (from-to)	7193-7196
Number of pages	4
Journal	Organic Letters
Volume	22
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.0c02529
State	Published - 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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10.1021/acs.orglett.0c02529

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abstract = "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.",

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AU - Song, Yang

AU - Parkin, Sean R.

AU - Anthony, John E.

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N2 - 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.

AB - 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.

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In Situ Reduction and Functionalization of Polycyclic Quinones

Abstract

Bibliographical note

ASJC Scopus subject areas

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