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Homolytic oxoalkylation of protonated N-heteroaromatic compounds

The oxoalkylation of pyridine, 2-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethylpyridines, quinoline, 4-methylquinoline, isoquinoline, and pyrazine with oxoalkyl radicals generated from 1-methylcyclobutanol or 1-methylcyclopentanol under the action of Pb(OAc)4 or Mn(OAc)3 has been carried out.The reaction products are isomers with 2-(6)- and 4-positions of the oxoalkyl group in the N-heteroaromatic ring.The isomer tatios have been determined as a function of the structure of the N-heteroaromatic compound and the reaction comditions. – Key words: homolytic oxoalkylation, heteroaromatic bases, lead tetraacetate, manganese triacetate, pyridine, quinoline, 1-methylcyclobutanol, 1-methylcyclopentanol.

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Reference：
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis—I. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis