Non-Metallic Carbene Pathway Transformations of Vinyl Diazo Compounds

doi:10.6023/cjoc202401018

Abstract

Vinyl diazo compounds are important compounds in organic synthesis. The generated vinyl metallic carbene species undergo insertion reactions, cycloaddition, and other reactions. As a class of weak nucleophiles, the reaction of vinyl diazo compounds with electron-deficient systems or free radicals not via metallic carbene intermediates has attracted attention from chemical societies in recent years. Carbene chemistry has been well investigated and reviewed. While the reactions of vinyl diazo compounds involved in the non-metallic carbene route are relatively scattered. Non-metallic carbene pathway transformations over the past two decades of vinyl diazo compounds are reviewed. Furthermore, the prospect in this field is also discussed.

Key words: vinyl diazo compounds, non metal carbene mechanism, cycloaddition, radical reaction

Cite this article

Jia-Xi Jiang, Quan-Zhong Liu. Non-Metallic Carbene Pathway Transformations of Vinyl Diazo Compounds[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2640-2657.

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Fig. & Tab. 36

Scheme 1. Reactivity profile of diazo compounds

Scheme 2. Preparation of vinyl diazo compounds

Scheme 3. Br?nsted acid catalysed Friedel-Crafts alkylation of vinyl diazo compounds with electron enriched arenes

Scheme 4. Oxidative rearrangement of vinyl diazo compounds

Scheme 5. Cyclization of vinyl diazoacetates and tert-butyl nitrite

Scheme 6. Cycloaddition of vinyl diazo compounds and in situ formed copper-carbene

Scheme 7. Copper catalysed enantioselective cycloaddition of vinyl diazo compounds

Scheme 8. Capture of metallic nitrene with vinyl diazo compounds

Scheme 9. Cycloaddition of zinc carbene with vinyl diazo compounds

Scheme 10. Scandium catalysed Mukaiyama-Aldol reaction of silyl enolate diazo compounds with aldehydes

Scheme 11. Gold catalysed reaction of vinyl diazo compounds with acetals

Scheme 12. TfOH catalysed Poparov rearrangement of arylimines and vinyl diazo compounds [L=P(tBu)2(o-biphenyl)]

Scheme 13. Gold catalyzed reaction quinoline N-oxides with vinyl diazo compounds

Scheme 14. Lewis acid catalysed addition of enol diazo compounds with enones

Scheme 15. TBSOTf catalysed Mukaiyama-aldol reaction of vinyl diazo compounds with enones

Scheme 16. Zinc triflate catalysed Mukaiyama-conjugate reaction of silyl enolate diazo compounds with enones

Scheme 17. Reactions of vinyl diazo compounds with quinone oxonium ions, quinone imine ketals, and Eschenmoser’s salt

Scheme 18. Gold catalysed [3＋2] cycloaddition of in situ formed nitrones with vinyl diazo compounds

Scheme 19. B(C6F5)3?catalysed diastereoselective reactions of vinyl diazo esters with nitrones

Scheme 20. Gold catalysed annulations of 2-alkynylbenzaldehydes with vinyl diazo compounds

Scheme 21. Gold catalysed [4＋2] cycloaddition/re-arrangement of vinyl diazo compunds with 2-alkynyl benzaldehyde

Scheme 22. Br?nsted acid catalysed reaction of 1H-isochromene acetals with vinyl diazo compounds

Scheme 23. Gold(I)-catalysed reactions between N?(o?alkynylphenyl)imines and vinyl diazo aryl ketones

Scheme 24. Gold catalysed reactions between enynones and vinyl diazo ketones

Scheme 25. Sc(OTf)3 catalyzed annulation of vinyl diazo compound with 3-sulphonyl indoles

Scheme 26. Inverse-electron-demand aza-Diels-Alder reaction of vinyl diazo compound and benzofuran-derived azadienes

Scheme 27. Light promoted radical 1,3-addition of perfluoroalkyl iodides to vinyl-diazoacetates

Scheme 28. Light-driven radical 1,3-selenosulfonylation of vinyl diazo compounds

Scheme 29. Light catalysed radical cyclization of vinyl diazo compounds with electron enriched olefins

Scheme 30. Iron catalyzed cycloaddition of vinyl diazo compound with electron enriched alkenes

Scheme 31. Visible-light-promoted radical tandem cyclization of N-aryl chloro difluoromethyl alkynyl ketoimines with vinyl diazo compounds

Scheme 32. Visible-light-promoted radical tandem cyclization of bromo difluoromethyl alkynyl ketones with vinyl diazo compounds

Scheme 33. Photocatalysed [3＋2] cycloaddition between indoles with vinyl diazo compounds

Scheme 34. Photocatalytic self [3＋2] cycloaddition of vinyl diazo compounds

Scheme 35. Photocatalytic ene reaction of vinyl diazo compounds with bicyclo[1,1,0] butanes

Scheme 36. Photocatalytic radical cyclization of N-heterocyclic carbene-borane complexes with vinyl diazo compounds

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