Metal-free C(sp(3))-H bond sulfonyloxylation of 2-alkylpyridines and alkylnitrones

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 -tosylated ketones after hydrolysis. Substitution reactions with nucleophiles then lead to diverse useful functionalizations for the synthesis of pincer ligands.
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Chang-Sheng Wang, Pierre H. Dixneuf, Jean-François Soulé. Metal-free C(sp(3))-H bond sulfonyloxylation of 2-alkylpyridines and alkylnitrones. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2018, 16 (27), pp.4954-4957. ⟨10.1039/c8ob01075g⟩. ⟨hal-01863970⟩

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