Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2013 Jun;8(6):1042-7.
doi: 10.1038/nprot.2013.059. Epub 2013 May 2.

Preparation and purification of zinc sulfinate reagents for drug discovery

Fionn O'Hara  1 , Ryan D Baxter, Alexander G O'Brien, Michael R Collins, Janice A Dixon, Yuta Fujiwara, Yoshihiro Ishihara, Phil S Baran
Affiliations

Preparation and purification of zinc sulfinate reagents for drug discovery

Fionn O'Hara et al. Nat Protoc. 2013 Jun.

Abstract

The present protocol details the synthesis of zinc bis(alkanesulfinate)s that can be used as general reagents for the formation of radical species. The zinc sulfinates described herein are generated from the corresponding sulfonyl chlorides by treatment with zinc dust. The products may be used crude, or a simple purification procedure may be performed to minimize incorporation of water and zinc chloride. Although the synthesis of the zinc sulfinate salts can generally be completed within 3 h, workup can take up to 24 h and purification can take up to 3 h. Following the steps in this protocol would enable the user to generate a small toolkit of zinc sulfinate reagents over the course of 1 week.

PubMed Disclaimer

Conflict of interest statement

COMPETING FINANCIAL INTERESTS

The authors declare no competing financial interests.

Figures

Figure 1
Figure 1
Heterocycle functionalization using recently developed and commercialized zinc bis(alkanesulphinate) reagents.
Figure 2
Figure 2
The focus of this article: the synthesis of zinc bis(alkanesulphinate) reagents.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Ji Y, et al. Innate C–H trifluoromethylation of heterocycles. Proc Natl Acad Sci. 2011;108:14411–14415. - PMC - PubMed
    1. Brückl T, Baxter RD, Ishihara Y, Baran PS. Innate and guided C–H functionalization logic. Acc Chem Res. 2012;45:826–839. - PMC - PubMed
    1. Fujiwara Y, et al. A new reagent for direct difluoromethylation. J Am Chem Soc. 2012;134:1494–1497. - PMC - PubMed
    1. Fujiwara Y, et al. Practical and innate carbon–hydrogen functionalization of heterocycles. Nature. 2012;492:95–99. - PMC - PubMed
    1. Weidner JP, Block SS. Infrared spectra of zinc sulfinates. Appl Spectroscopy. 1969;23:337–341.

Publication types

MeSH terms