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
Review
. 2016 Oct 5;138(39):12692-12714.
doi: 10.1021/jacs.6b08856. Epub 2016 Sep 26.

Radicals: Reactive Intermediates with Translational Potential

Affiliations
Review

Radicals: Reactive Intermediates with Translational Potential

Ming Yan et al. J Am Chem Soc. .

Abstract

This Perspective illustrates the defining characteristics of free radical chemistry, beginning with its rich and storied history. Studies from our laboratory are discussed along with recent developments emanating from others in this burgeoning area. The practicality and chemoselectivity of radical reactions enable rapid access to molecules of relevance to drug discovery, agrochemistry, material science, and other disciplines. Thus, these reactive intermediates possess inherent translational potential, as they can be widely used to expedite scientific endeavors for the betterment of humankind.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Selected milestones in radical chemistry.
Figure 2
Figure 2
Evolution of enolate oxidative coupling in our laboratory and its synthetic applications.
Figure 3
Figure 3
Development and applications of the borono-Minisci reaction.
Figure 4
Figure 4
Development and applications of sulfinate reagents as enabling radical precursors in biomedical research.
Figure 5
Figure 5
Olefins as latent radicals: applications to C–C and C–N bond construction.
Figure 6
Figure 6
Development of redox-active esters (RAEs) as radical precursors in cross-coupling reactions.
Figure 7
Figure 7
Radical chemistry: selected highlights from the past 5 years that capitalize on the unique power of these reactive intermediates.
Figure 8
Figure 8
Revisiting the persistent radical effect (PRE).

References

    1. Carey F. A.; Giuliano R. M.. Organic Chemistry, 10th ed.; McGraw-Hill Education: New York, 2016.
    2. Wade L. G.Organic Chemistry, 8th ed.; Pearson: New York, 2011.
    3. McMurry J.Organic Chemistry, 9th ed.; Cengage Learning: Boston, 2015.
    4. Clayden J.; Greeves N.; Warren S.. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012.
    1. Walling C. Tetrahedron 1985, 41, 3887. 10.1016/S0040-4020(01)97172-8. - DOI
    2. Ingold K. U. Pure Appl. Chem. 1997, 69, 241. 10.1351/pac199769020241. - DOI
    1. For selected general reviews of radical chemistry, see:

    2. Kochi J. K., Ed. Free Radicals, Vol. 1: Dynamics of Elementary Processes; Wiley-Interscience: New York, 1973.
    3. Curran D. P. Synthesis 1988, 6, 417. 10.1055/s-1988-27600. - DOI
    4. Curran D. P. Synthesis 1988, 7, 489. 10.1055/s-1988-27620. - DOI
    5. Jasperse C. P.; Curran D. P.; Fevig T. L. Chem. Rev. 1991, 91, 1237. 10.1021/cr00006a006. - DOI
    6. Radicals in Organic Synthesis, 1st ed.; Renaud P., Sibi M., Eds.; Wiley-VCH: Weinheim, 2001.
    7. Togo H.Advanced Free Radical Reactions for Organic Synthesis; Elsevier: Amsterdam, 2003.
    8. Zard S. Z.Radical Reactions in Organic Synthesis; Oxford University Press: Oxford, 2003.
    1. Kolbe H. Ann. Chem. Pharm. 1848, 64, 339. 10.1002/jlac.18480640346. - DOI
    1. Borodin A. Ann. Chem. Pharm. 1861, 119, 121. 10.1002/jlac.18611190113. - DOI
    2. Hunsdiecker H.; Hunsdiecker C. Ber. Dtsch. Chem. Ges. B 1942, 75, 291. 10.1002/cber.19420750309. - DOI

Publication types

MeSH terms