Efficient and scalable synthesis of 3,4-dihydroisoquinolin-1(2H)-ones by benzylic oxidation of tetrahydroisoquinoline derivatives using cerium ammonium nitrate (CAN),Organic & Biomolecular Chemistry

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Efficient and scalable synthesis of 3,4-dihydroisoquinolin-1(2H)-ones by benzylic oxidation of tetrahydroisoquinoline derivatives using cerium ammonium nitrate (CAN)
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2024-04-26 , DOI: 10.1039/d4ob00491d
Jiajun Luo ₁ , Zhilong Li ₁ , Jiaxin He ₁ , Tong Li ₁ , Daochen Wu ₁ , Yang Lai ₁ , Haiying Sun ₁

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An efficient and scalable method for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones through benzylic oxidation of tetrahydroisoquinoline derivatives using a catalytic amount of cerium ammonium nitrate (CAN) and a stoichiometric amount of NaBrO₃ as oxidants was developed. The reaction is significantly influenced by the substituent groups on the phenyl ring. While electron-withdrawing groups on the phenyl ring can lower the reactivities of the substrates, electron-donating groups on the phenyl ring can dramatically promote the oxidation rate.

中文翻译：

使用硝酸铈铵 (CAN) 通过四氢异喹啉衍生物的苄基氧化高效且可规模化合成 3,4-二氢异喹啉-1(2H)-酮

开发了一种高效且可扩展的方法，通过使用催化量的硝酸铈铵 (CAN) 和化学计量的 NaBrO ₃作为氧化剂，通过四氢异喹啉衍生物的苄基氧化来合成 3,4-二氢异喹啉-1( 2 H )-酮。该反应受苯环上的取代基的显着影响。虽然苯环上的吸电子基团可以降低底物的反应活性，但苯环上的给电子基团可以显着促进氧化速率。

更新日期：2024-04-26

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