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A highly efficient metal-free oxidative direct C(sp 3 )–H functionalization of  N -acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines (THIQs) with a wide range of electron-rich nucleophiles was accomplished under mild conditions through oxidation with DDQ and subsequent trapping of the resulting reactive and stable  N -acyl/sulfonyl iminium ions. The synthetic utility of this method was illustrated by a concise and efficient total synthesis of (±)-benzo[ a ]quinolizidine ( 10 ) in 3 steps from the known  N -Cbz 1,2,3,4-THIQ  4b .

frontiers in chemistry

Direct and Efficient C(sp3)–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation