Advances in Organophosphorus Redox Catalysis

doi:10.6023/cjoc202106004

Abstract

Organophosphorus reagents play very important role in organic synthesis. The development of Wittig reaction, Staudinger reaction, Appel reaction and Mitsunobu reaction mediated by phosphine compounds is of great significance in scientific research and industrial production. In recent decades, the research on the design of P(III)/P(V) redox catalysis and catalysts to realize the catalytic mode of these reactions, and avoiding the production of stoichiometric R₃P=O has developed rapidly. This review introduces the research progress of the catalytic process of each reaction in turn. The future research direction in this field about the reactions involving stoichiometric R₃P=O is prospected.

Key words: Wittig reaction, Staudinger reaction, Appel reaction, Mitsunobu reaction, phosphine catalysis, P(III)/P(V) redox catalysis

Cite this article

Wei Cai, You Huang. Advances in Organophosphorus Redox Catalysis[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3903-3913.

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Fig. & Tab. 32

Scheme 1. Stoichiometric phosphine mediated name reactions

Scheme 2. Catalytic Wittig reaction with stabilized ylides

Scheme 3. Catalytic Wittig reaction in room temperature

Scheme 4. Catalytic Wittig reaction with unstabilized ylides

Scheme 5. A tandem Wittig/conjugate-reduction reaction.

Scheme 6. Catalytic Wittig reaction with high tension precatalyst

Scheme 7. Catalytic Wittig reaction with bisphosphine catalyst

Scheme 8. Other ylide precursors and catalytic Wittig reaction modes

Scheme 9. Asymmetric catalytic Wittig reaction

Scheme 10. Catalytic Staudinger reaction

Scheme 11. PPh3-mediated catalytic Staudinger reaction

Scheme 12. Catalytic Staudinger amidation reaction

Scheme 13. Catalytic Staudinger-Aza-Wittig reaction

Scheme 14. PPh3-mediated catalytic Staudinger-Aza-Wittig rea- ction

Scheme 15. One-pot catalytic Staudinger-Aza-Wittig reaction

Scheme 16. Catalytic aza-Wittig reaction of diazonium compounds

Scheme 17. Catalytic enantioselective aza-Wittig reaction

Scheme 18. Catalytic Appel bromination reaction

Scheme 19. Catalytic Appel chlorination reaction

Scheme 20. Catalytic Appel amidation reaction

Scheme 21. Phosphetane-mediated tandem annulation reaction

Scheme 22. Catalytic Mitsunobu reaction

Scheme 23. Recycling both phosphine oxide and the azocarboxylate reagent

Scheme 24. Redox-neutral catalytic Mitsunobu reaction

Scheme 25. Catalytic reductive O-atom transfer

Scheme 26. Phosphetane-mediated catalytic deoxygenative condensation reaction

Scheme 27. Phosphetane-mediated Cadogan heterocyclization reaction

Scheme 28. Phosphetane-mediated C—H amination/cyclization reaction

Scheme 29. Phosphetane-mediated reductive C—N cross-coupling

Scheme 30. Phosphetane-mediated tandem reaction

Scheme 31. Phosphine-mediated reductive sulfhydrylation

Scheme 32. Phosphine-mediated hydrogenation reduction

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