Palladation of 8-methylquinoline and related 2-substituted derivatives: evidence for in-plane metallation of methyl groups

Abstract
8-Methylquinoline reacts with palladium acetate to give palladation at the 8-methyl group and similar metallations occur for 2-substituted derivatives where one would expect the substituent R to allow chelate ring formation (R = CH:NMe, CO2H, or CH2OH) but not where R = Me, Br, or CHO; evidence is presented for metallation occurring when the ligand plane and the co-ordination plane are coincident.

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