Visible Light Driving Alkene Difunctionalization Reaction Involving Group Migration

doi:10.6023/cjoc202207037

Abstract

As an important synthetic method in organic chemistry research, the difunctionalization of alkenes plays an important role in the field of synthetic chemistry. In recent years, the difunctionalization of alkenes caused by free radicals participating in the migration of intramolecular functional groups has risen rapidly, providing a new idea for the difunctionalization of alkenes. This strategy has the advantages of atom economy and environmental friendliness. As an effective means to generate radical precursors, mild and green photocatalysis has inspired chemistsʼ interest in initiating difunctionalization of alkenes by using photocatalysis to drive group migration. According to the species of near and far aryl, heteroaryl, imine, cyano, acyl, alkynyl, alkenyl and other functional groups involved in photocatalytic radicals, the alkene difunctionalization reactions are classified and summarized, and some reaction mechanisms are discussed.

Key words: visible-light photoredox, radical, migration, alkene, difunctionalization

Cite this article

Meng Li, Dongyang Zhao, Kai Sun. Visible Light Driving Alkene Difunctionalization Reaction Involving Group Migration[J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4152-4168.

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Fig. & Tab. 38

Scheme 1. Construction of amine compounds with quaternary carbon structures under blue LED

Scheme 2. Construction of benzofuran compounds under visible light

Scheme 3. Construction of α-aryl-β-alkyl ketones under blue LED

Scheme 4. Construction of the 1,5-dicarbonyl compounds under visible light

Scheme 5. Construction of the difluoro 1,5-dicarbonyl compounds under blue LEDs

Scheme 6. Construction of β-aryl-γ-ketophosphine oxides under blue LED

Scheme 7. Construction of α-aryl-γ-methylsulfinyl ketones under blue LED

Scheme 8. Construction of β-trifluoromethyl-α-aryl ketones under blue LED

Scheme 9. Construction of β-trifluoromethyl-α-aryl ketones under blue LED

Scheme 10. Construction of γ-cyano ketones under blue LED

Scheme 11. Construction of γ-oxo-phosphonate under blue LED

Scheme 12. Construction of 1,5-diketones under blue LED

Scheme 13. Construction of β-drifluoromethyl-α-aryl ketones under blue LED

Scheme 14. Construction of perfluoroalkylated compounds under blue LED

Scheme 15. Construction of the cyclic ketones under visible light

Scheme 16. Construction of 1,4-dicarbonyl compounds under visible light

Scheme 17. Construction of difluoromethylated cyclopentanone under blue LED

Scheme 18. Construction of β-sulfonated cyclopentanones under blue LEDs

Scheme 19. Construction of β-difluorinated-α-pyridone under blue LED

Scheme 20. Construction of 1,2-diboronic esters under blue LED

Scheme 21. Construction of α-aryl-β-trifluor-omethyl amides and CF3-containing oxindoles/isoquinolinediones under visible light

Scheme 22. Construction of α-aryl-β-trifluoromethylamides under visible light

Scheme 23. Construction of perfluorinated indoles or α-aryl- β-fluoroalkylamides under visible light

Scheme 24. Construction of α-trifluoromethylated ketones under visible light

Scheme 25. Construction of difluoroalkylated tetracycles under blue LED

Scheme 26. Construction of 2,2-diarylethylamine compounds under blue LED

Scheme 27. Construction of difluoroalkylated benzothiazoles under blue LED

Scheme 28. Construction of difluoroester amides under visible light

Scheme 29. Construction of di-/mono-fluorinated alkyl ketones under visible light

Scheme 30. Construction of difluoroalkylated alkynyl ketones under blue LED

Scheme 31. Construction of benzothiazolones under blue LED

Scheme 32. Construction of heteroaryl- and oximino-substituted alkyl sulfones under blue LEDs

Scheme 33. Construction of cyclopentane carboxylates under visible light

Scheme 34. Construction of cyclohexene under visible light

Scheme 35. Construction of di- and mono-fluorinated alkyl nitriles under blue LED

Scheme 36. Construction of perfluoroalkylated ketones under blue LED

Scheme 37. Construction of imino alcohols under visible light

Scheme 38. Construction of difluoroalkylated/phosphonylated α,α-diarylalkylureas under visible light

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可见光驱动基团迁移引发的烯烃双官能团化反应