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

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

1 Scopus citations

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

Publisher Copyright:
© 2020 American Chemical Society.

Funding

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).

Funders	Funder number
National Science Foundation (NSF)	CHE-0319176, CHE-1625732
Michigan State University-U.S. Department of Energy (MSU-DOE) Plant Research Laboratory
Office of Basic Energy Sciences	ERW7404

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c02529

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title = "In Situ Reduction and Functionalization of Polycyclic Quinones",

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.",

author = "Thorley, {Karl J.} and Yang Song and Parkin, {Sean R.} and Anthony, {John E.}",

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AU - Parkin, Sean R.

AU - Anthony, John E.

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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

Funding

ASJC Scopus subject areas

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