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Issue 27, 2018
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Metal-free C(sp3)–H bond sulfonyloxylation of 2-alkylpyridines and alkylnitrones

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Abstract

Pyridin-2-ylmethyl tosylate derivatives are obtained in high yields from 2-alkylpyridine 1-oxides via a [3,3]-sigmatropic rearrangement of the adduct between 2-alkylpridine 1-oxides with benzenesulfonyl chlorides. Moreover, alkylnitrones also undergo [3,3]-sigmatropic rearrangement to give α-tosylated ketones after hydrolysis. Substitution reactions with nucleophiles then lead to diverse useful functionalizations for the synthesis of pincer ligands.

Graphical abstract: Metal-free C(sp3)–H bond sulfonyloxylation of 2-alkylpyridines and alkylnitrones

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Publication details

The article was received on 08 May 2018, accepted on 16 Jun 2018 and first published on 18 Jun 2018


Article type: Communication
DOI: 10.1039/C8OB01075G
Citation: Org. Biomol. Chem., 2018,16, 4954-4957
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    Metal-free C(sp3)–H bond sulfonyloxylation of 2-alkylpyridines and alkylnitrones

    C. Wang, P. H. Dixneuf and J. Soulé, Org. Biomol. Chem., 2018, 16, 4954
    DOI: 10.1039/C8OB01075G

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