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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.

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

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