Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate

doi:10.6023/cjoc202109040

Abstract

Carbene is one of the most important synthetic intermediates in organic synthesis. In the past few decades, transition-metal catalyzed carbene transfer reactions have made remarkable development. Recently, visible light-promoted transformation of diazo compounds through the formation of free carbene as key intermediate begun to rise. The reaction only need visible light as the sole energy source which meets the concept of green chemistry. Since the pioneering works developed by the groups of Diaves and Zhou, photo-promoted transformation of diazo compounds has attracted more and more attentions. On the basis of previous work, the latest progress in this field is further improved, which mainly focuses on the recent new transformation reactions of diazo compounds under visible light irradiation and the contributions reported from Chinese research group. The future development direction, as well as challenges in this field is prospected.

Key words: visible light, diazo compound, carbene, green chemistry

Cite this article

Baogui Cai, Jun Xuan. Visible Light-Promoted Transformation of Diazo Compounds via the Formation of Free Carbene as Key Intermediate[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4565-4574.

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Fig. & Tab. 23

Scheme 1. Absorption range of diverse diazo compounds

Scheme 2. Visible light induced cyclopropanation of aryldiazoacetates with styrene

Scheme 3. Visible light induced cyclopropanation of diazooxindoles with arenes

Scheme 4. Photochemical cyclopropanation under continuous flow conditions

Scheme 5. Visible light promoted reaction of aryldiazoacetates with indole derivatives

Scheme 6. Visible light promoted insertion of carbene into X—H bond

Scheme 7. Visible light promoted insertion of carbene into oximes

Scheme 8. Visible light promoted multicomponent reactions involving aryldiazoacetates

Scheme 9. Visible light and base promoted synthesis of benzofuran derivatives

Scheme 10. Visible light promoted O-alkylation 2-pyridinone

Scheme 11. Visible light and base promoted reaction of hydrazone compounds with aromatic amines

Scheme 12. Visible light promoted N1-alkylation of aryldiazoacetates with benzotriazoles

Scheme 13. Visible light S—H bond insertion reaction

Scheme 14. Visible light promoted Doyle-Kirmse reaction

Scheme 15. Visible light promoted reaction of aryldiazoacetates with difluoroallyl sulfides

Scheme 16. Visible light promoted synthesis of sulfoxonium ylides

Scheme 17. Visible light promoted reaction of 4-diazo-1,4- dihydroisoquinolin-3-ones with allyl/propargyl sulfide

Scheme 18. Visible light induced multicomponent reactions of aryldiazoacetates, amines and carbon dioxide

Scheme 19. Visible light promoted multicomponent reaction of aryldiazoacetates, oximes and tetrahydrofurans

Scheme 20. Visible light promoted in situ generation/ rearrangement of nitrones to construct amide bonds

Scheme 21. Selective synthesis of aziridine and imidazolidine promoted by visible light

Scheme 22. Visible light promoted reaction of aryldiazoacetates with o-aminoacetophenones

Scheme 23. Visible light promoted coupling of diazo compounds

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