Visible-Light-Mediated C-2 Functionalization and Deoxygenative Strategies in Heterocyclic N-Oxides,Advanced Synthesis & Catalysis

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Visible-Light-Mediated C-2 Functionalization and Deoxygenative Strategies in Heterocyclic N-Oxides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-06-01 , DOI: 10.1002/adsc.202200200
Jitender Singh ₁ , Roshan I. Patel ₂ , Anuj Sharma ₁

Affiliation

Heterocyclic N-oxides are prevalent in numerous natural products with broad applications in pharmaceuticals, agrochemicals, material sciences, and asymmetric synthesis. Owing to their profound biological and physiological activity and unique chemical reactivity, the importance of these compounds has stimulated substantial interest among organic synthetic chemists. More importantly, C-2 functionalization of heterocyclic N-oxides, including pyridine-, isoquinoline-, pyrazine-, quinoxaline-, and quinoline N-oxides, is among the most important strategies for heterocyclic functionalization. Besides, deoxygenation of heterocyclic N-oxides has also emerged as a reaction of significance in organic chemistry. In the past decade, visible light photoredox catalyzed C-2 functionalization and deoxygenation of these heterocyclic N-oxides have drawn substantial attention owing to their mild reaction conditions. This review has been categorized based on visible-light-mediated nondeoxygenative C-2 functionalization (alkylation, fluoroalkylation, arylation, acylation, and amination), deoxygenative C-2 functionalization (sulfonylation, alkynylation, alkylation, and acylation), and deoxygenation (without C−H functionalization) of heterocyclic N-oxides. For most part of the work, the substrate scope, limitation, and mechanism of the reactions have been discussed.

中文翻译：

杂环 N-氧化物中可见光介导的 C-2 功能化和脱氧策略

杂环N-氧化物普遍存在于许多天然产物中，在药物、农用化学品、材料科学和不对称合成中具有广泛的应用。由于它们深厚的生物和生理活性以及独特的化学反应性，这些化合物的重要性引起了有机合成化学家的极大兴趣。更重要的是，杂环N-氧化物（包括吡啶-、异喹啉-、吡嗪-、喹喔啉-和喹啉N-氧化物）的 C-2 官能化是杂环官能化最重要的策略之一。此外，杂环N的脱氧-氧化物也已成为有机化学中重要的反应。在过去的十年中，可见光光氧化还原催化的这些杂环N-氧化物的C-2功能化和脱氧由于其温和的反应条件而引起了广泛关注。这篇综述根据可见光介导的非脱氧 C-2 官能化（烷基化、氟烷基化、芳基化、酰化和胺化）、脱氧 C-2 官能化（磺酰化、炔基化、烷基化和酰化）和脱氧（无杂环N-氧化物的C-H官能化）。对于大部分工作，已经讨论了反应的底物范围、限制和机理。

更新日期：2022-06-01

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