A highly efficient metal-free oxidative direct C(sp³)–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.

中文翻译：

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N-酰基/磺酰基四氢异喹啉（THIQs）通过2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone（DDQ）氧化直接和高效的N-酰基/磺酰基四氢异喹啉（THIQs）与富电子亲核试剂。

高效的无金属氧化直接C（sp ³）–H官能化ñ通过使用DDQ进行氧化并随后捕获所得的反应性和稳定性，可在温和条件下制备具有多种富电子亲核体的-酰基/磺酰基1,2,3,4-四氢异喹啉（THIQs） ñ-酰基/磺酰基亚胺离子。该方法的合成效用通过简明高效的（±）-苯并[一种]喹oli嗪（10），距离已知的3步 ñ-Cbz 1,2,3,4-THIQ 4b。