Asymmetric Photocatalytic Synthesis of Enantioenriched Azaarene Derivatives

doi:10.6023/cjoc202201047

Abstract

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

Cite this article

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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Fig. & Tab. 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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