可见光不对称催化合成手性氮杂芳烃衍生物

doi:10.6023/cjoc202201047

摘要/Abstract

氮杂芳烃衍生物在众多领域尤其是医药和材料工业中的重要性吸引了化学家对发展其高效合成方法的持续关注. 迄今, 以市售氮杂芳烃或其简单衍生物作为原料, 且利用氮杂芳烃的电子性质引发化学转化的官能团化策略已被认为是一种强有力的工具. 其中, 由于具有条件温和、官能团耐受性良好且反应形式多样等优点, 可见光驱动光催化的方法被广泛探索. 值得注意的是, 许多针对含亚胺氮杂芳烃衍生物合成的反应类型的不对称版本被成功开发, 所获得的对映体纯产物具有令人满意的结果. 依据所构建手性中心相对氮杂芳烃的位置分四个部分总结, 并讨论这一重要领域的发展.

关键词: 可见光, 不对称光催化, 自由基加成, 质子化, 氮杂芳烃

The importance of azaarene derivatives in many arenas, especially pharmaceutical and material industry, has attracted increasing attention of chemists to develop highly efficient synthetic methods. To date, functionalization of commercially available azaarenes and their simple derivatives as feedstocks by exploiting the electronic properties of azaarenes to trigger transformations has been appreciated as a powerful tool. Among them, due to the advantages of mild reaction conditions, good functional group tolerance and diverse reaction types, the methods via visible light-driven photocatalysis have been extensively explored. Notably, a number of asymmetric manifolds towards the synthesis of enantioenriched imine-containing azaarene derivatives have been established with satisfactory results. The advances of this important area are summarized and discussed according to the relative positions of the formed stereocenters to azaarenes.

Key words: visible light, asymmetric photocatalysis, radical addition, protonation, azaarene

引用此文

尹艳丽, 赵筱薇, 江智勇. 可见光不对称催化合成手性氮杂芳烃衍生物[J]. 有机化学, 2022, 42(6): 1609-1625.

Yanli Yin, Xiaowei Zhao, Zhiyong Jiang. Asymmetric Photocatalytic Synthesis of Enantioenriched Azaarene Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1609-1625.

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图/表 16

Scheme 1. Fundamental protocols of synthesizing azaarene derivatives

Figure 1. Classification of azaarenes

Scheme 2. Enantioselective Minisci-type reaction via cooperative metallophotoredox and chiral Brønsted acid catalysis

Scheme 3. Enantioselective Minisci-type reaction via cooperative organophotoredox and chiral Brønsted acid catalysis

Scheme 4. Three-component asymmetric Minisci-type reactions

Scheme 5. Hydrogen atom transfer-enabled enantioselective Minisci-type reactions of amides

Scheme 6. Radical addition-enantioselective protonation via cooperative photoredox and chiral Brønsted acid catalysis

Scheme 7. Radical addition-enantioselective protonation via cooperative HAT and chiral Brønsted acid catalysis

Scheme 8. Single-electron reduction-enantioselective protonation

Scheme 9. Asymmetric olefin difunctionalization to assemble all-carbon quaternary stereocenters α to azaarenes

Scheme 10. Enantioselective α-alkylation of aldehydes with heteroaryl methylene bromides

Scheme 11. Asymmetric radical addition of α-amino radicals to alkenylazaarenes: the pioneering result

Scheme 12. Capitalizing on non-classic H-bonding strategy to supplement chiral bifunctional H-bonding catalysis

Scheme 13. Enantioselective intermolecular reductive coupling of carbonyls and imines with vinylpyridines

Scheme 14. Enantioselective Beckwith-Enholm cyclizations to divergent asymmetric synthesis of azaarene-functionalized cyclic alcohols

Scheme 15. Reductive cross coupling and enantioselective protonation of olefins to construct stereocenters δ to azaarenes

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