Abstract

Abstract Organic reactions involving radical cation and radical anion intermediates are synthetically powerful umpolung processes that enable electronically mismatched couplings between pairs of electron‐rich or pairs of electron‐poor organic fragments. Nevertheless, the adoption of these reactions as synthetic methods has been relatively slow in comparison with that of reactions involving more conventional reactive intermediates such as carbanions, carbocations, and neutral radicals. This Microreview provides a brief survey of radical ion chemistry and highlights the use of transition metal photocatalysis as a convenient means to investigate radical‐ion‐mediated transformations.

Keywords

ChemistryUmpolungCarbocationRadicalCarbanionRadical ionReactive intermediateOrganic reactionPhotochemistryIonFree-radical reactionOrganic chemistryCombinatorial chemistryComputational chemistryNucleophileCatalysis

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Publication Info

Year
2012
Type
article
Volume
2012
Issue
18
Pages
3359-3372
Citations
210
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Cite This

Michael A. Ischay, Tehshik P. Yoon (2012). Accessing the Synthetic Chemistry of Radical Ions. European Journal of Organic Chemistry , 2012 (18) , 3359-3372. https://doi.org/10.1002/ejoc.201101071

Identifiers

DOI
10.1002/ejoc.201101071

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Data completeness: 77%