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Molecules 2014, 19(10), 16190-16222; doi:10.3390/molecules191016190

Radical Addition to Iminium Ions and Cationic Heterocycles

Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10–14, 55128 Mainz, Germany
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Received: 28 August 2014 / Revised: 22 September 2014 / Accepted: 22 September 2014 / Published: 10 October 2014
(This article belongs to the Special Issue Free Radicals and Radical Ions)

Abstract

Carbon-centered radicals represent highly useful reactive intermediates in organic synthesis. Their nucleophilic character is reflected by fast additions to electron deficient C=X double bonds as present in iminium ions or cationic heterocycles. This review covers diverse reactions of preformed or in situ-generated cationic substrates with various types of C-radicals, including alkyl, alkoxyalkyl, trifluoromethyl, aryl, acyl, carbamoyl, and alkoxycarbonyl species. Despite its high reactivity, the strong interaction of the radical’s SOMO with the LUMO of the cation frequently results in a high regioselectivity. Intra- and intermolecular processes such as the Minisci reaction, the Porta reaction, and the Knabe rearrangement will be discussed along with transition metal and photoredox catalysis or electrochemical methods to generate the odd-electron species. View Full-Text
Keywords: radicals; iminium salts; heterocycles; addition reactions; rearrangements; Minisci reaction; Porta reaction; photoredox catalysis; transition metal catalysis; late-stage functionalization radicals; iminium salts; heterocycles; addition reactions; rearrangements; Minisci reaction; Porta reaction; photoredox catalysis; transition metal catalysis; late-stage functionalization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Tauber, J.; Imbri, D.; Opatz, T. Radical Addition to Iminium Ions and Cationic Heterocycles. Molecules 2014, 19, 16190-16222.

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