Photocatalytic Reactions Involving Diazo Compounds as Radical Precursors

doi:10.6023/cjoc202207016

Abstract

Diazo compounds are important synthons which have attracted condirable attentions by synthetic chemists. They can server as carbene precursors, 1,3-dipoles, C-nucleophiles, terminal N-electrophiles and radical intermediates. In recent years, the photocatalytic generation of radicals from diazo compounds has made remarkable development. In this review, the recent developments in this research field are summarized which mainly focus on the generation of diazomethyl radical, carbon radicals, carbyne radicals and allene radicals from diazo compounds. Moreover, the future development direction, as well as challenges in this field is prospected.

Key words: photoredox catalysis, diazo compounds, radical

Cite this article

Yang Xie, Jun Xuan. Photocatalytic Reactions Involving Diazo Compounds as Radical Precursors[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4247-4256.

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Fig. & Tab. 18

Scheme 1. Photoredox generation of carbyne equivalents

Scheme 2. Photoredox catalysis synthesis of oxadiazole with diazos iodine reagent

Scheme 3. Photoredox catalysis synthesis of oxadiazoles containing CF3

Scheme 4. Photoredox catalytic α-diazo sulfonium triflates synthesis of triazoles

Scheme 5. Asymmetric and photoredox catalysis of diazo compounds

Scheme 6. Iodine-catalyzed cyclopropanation of diazo compounds and alkenes

Scheme 7. Iodine-catalyzed cyclopropanation of diazo compounds and alkenes

Scheme 8. Visible light-promoted radical benzannulation of diazoketones

Scheme 9. Synthesis of functionalized naphthalene-1-ols under metal-free and visible light-mediated conditions

Scheme 10. Photocatalytic C2 alkylation of indole with ethyl diazoacetate

Scheme 11. Radical-mediated strategies for the functionalization of alkenes with diazo compounds

Scheme 12. Radical cascade multicomponent Minisci reactions with diazo compounds

Scheme 13. Visible-light-induced multicomponent synthesis of γ?amino esters with diazo compounds

Scheme 14. Combination of NHC catalysis and photocatalysis for bifunctionalization of olefins

Scheme 15. Visible-light-promoted aerobic oxyphosphorylation of α-diazoesters with H?phosphine oxides

Scheme 16. Photocatalytic 1,2-oxo-alkylation reaction of styrenes with diazoacetates

Scheme 17. Three component coupling of alkynes, α?diazo sulfonium triflate and water

Scheme 18. Synthesis of tetrasubstituted allenes via visible- light-promoted radical 1,3-difunctionalization of alkynyl diazo compounds

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