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Issue 48, 2019
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Double C–N bond cleavages of N-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides

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Abstract

In this paper, regiospecific, double intraannular C–N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S–Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C–N bond cleavages of N-alkyl 4-oxopiperidinium salt. The secondary amine thus produced was trapped by sulfonyl chloride to yield the desired sulfonamide product. The key feature of this protocol is that two intraannular C–N bonds of the 4-oxopiperidine ring are cleaved in one step under metal- and oxidant-free conditions.

Graphical abstract: Double C–N bond cleavages of N-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides

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Publication details

The article was received on 29 Sep 2019, accepted on 11 Nov 2019 and first published on 14 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02107H
Org. Biomol. Chem., 2019,17, 10172-10177

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    Double C–N bond cleavages of N-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides

    Y. Fu, M. Li, C. Shi, F. Li, Z. Du and C. Huo, Org. Biomol. Chem., 2019, 17, 10172
    DOI: 10.1039/C9OB02107H

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