Advances in Catalytic Asymmetric Hydrogen-Phosphine/Phosphorus Functionalization of Unsaturated Carbon-Carbon Bonds

doi:10.6023/cjoc202405046

Abstract

Phosphine/Phosphorus-containing chiral compounds have a wide range of applications in pharmaceuticals industry, agriculture, functionalized materials, and asymmetric catalysis. Accordingly, the development of efficient methods for the synthesis of structurally diverse phosphine/phosphorus-containing chiral compounds has attracted the attention of chemists. Among the multitude of synthetic strategies developed, catalytic asymmetric hydrogen-phosphine/phosphorus functiona- lization of unsaturated carbon-carbon bonds stands out as a particularly efficient and atom economical method. Utilizing this strategy, a wide array of phosphine/phosphorus-containing chiral compounds can be synthesized with remarkable efficiency. The state-of-the-art studies on catalytic asymmetric hydrogen-phosphine/phosphorus functionalization of unsaturated carbon- carbon bonds in past decade are summarized. Mechanistic insights, synthetic applications, as well as challenges and opportunities of this field are elucidated and discussed.

Key words: asymmetric catalysis, unsaturated carbon-carbon bond, hydrogen-phosphine/phosphorus functionalization, chiral phosphine/phosphorus-containing compound, phosphine/phosphorus reagent

Cite this article

Tingjia Sun, Guoyin Sun, Wei Sun, Xuesong Peng, Juan Liao, Yong You, Weicheng Yuan. Advances in Catalytic Asymmetric Hydrogen-Phosphine/Phosphorus Functionalization of Unsaturated Carbon-Carbon Bonds[J]. Chinese Journal of Organic Chemistry, 2024, 44(12): 3647-3677.

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Fig. & Tab. 51

Figure 1. Selected phosphine/phosphorus-containing bioactive molecules and chiral ligands

Scheme 1. Catalytic asymmetric hydrogen-phosphine/phosphorus functionalization for the synthesis of chiral phosphine/phosphorus- containing compounds

Scheme 2. Pioneering works of catalytic asymmetric hydrophosphination reaction

Scheme 3. Various phosphine/phosphorus reagents for catalytic asymmetric hydrogen-phosphine/phosphorus functionalization

Scheme 4. Ni-catalyzed asymmetric hydrophosphination of α,β-unsaturated ketones and primary phosphines

Scheme 5. Pincer-Pd-catalyzed asymmetric hydrophosphination of α,β-unsaturated ketones and secondary phosphines

Scheme 6. NHC-copper-catalyzed asymmetric hydrophosphination of diarylphosphines and α,β-unsaturated ketones

Scheme 7. Pd-catalyzed asymmetric hydrophosphination of diarylphosphines and α,β-unsaturated amides

Scheme 8. Pd-catalyzed asymmetric hydrophosphination of diarylphosphines and β,γ-unsaturated α-ketoesters

Scheme 9. Copper-catalyzed asymmetric 1,4-hydrophosphination of α,β-unsaturated phosphine sulfides

Scheme 10. Synthesis of chiral 1,2-bisphosphines and their application in Rh-catalyzed asymmetric hydrogenation

Scheme 11. Copper-catalyzed asymmetric hydrophosphination of α,β-unsaturated amides

Scheme 12. Proposed mechanism of copper-catalyzed asymmetric hydrophosphination of α,β-unsaturated amides

Scheme 13. Manganese-catalyzed asymmetric hydrophosphination of α,β-unsaturated compounds

Scheme 14. Proposed mechanism of manganese-catalyzed asymmetric hydrophosphination of α,β-unsaturated compounds

Scheme 15. Nickel-catalyzed asymmetric hydrophosphination of α,β-unsaturated ketones and diarylphosphines

Scheme 16. Pd-catalyzed asymmetric hydrophosphination of gem-difluoroallenes and diarylphosphines

Scheme 17. Copper-catalyzed asymmetric hydrophosphination of alkenyl isoquinolines

Scheme 18. Manganese-catalyzed asymmetric hydrophosphination of terminal alkenyl aza-heteroarenes

Scheme 19. Palladium-catalyzed asymmetric 1,6-hydrophosphination of diarylphosphines and α,β,γ,δ-unsaturated compounds

Scheme 20. Pd-catalyzed asymmetric 1,6-hydrophosphination of benzoquinones and diarylphosphines

Scheme 21. Pd-catalyzed asymmetric hydrophosphination of achiral heterobicyclic alkenes and diarylphosphines

Scheme 22. Pd-catalyzed asymmetric hydrophosphination of cyclopropenes and diarylphosphines

Scheme 23. La-catalyzed asymmetric hydrophosphinylation of cyclopropenes and diarylphosphines

Scheme 24. Cu-catalyzed asymmetric hydrophosphination of cyclopropenes and diarylphosphines

Scheme 25. Synthesis of chiral phosphine-olefin ligands and their application in transition metal-catalysis

Scheme 26. Pd-catalyzed asymmetric hydrophosphination of internal alkynes and secondary phosphines

Scheme 27. Cobalt-catalyzed asymmetric hydrophosphinylation of ethyl acrylate and phosphine oxides

Scheme 28. Cobalt-catalyzed asymmetric hydrophosphinylation of imidazolyl-directed α,β-unsaturated amides and phosphine oxides

Scheme 29. Pd- and Ni-catalyzed asymmetric hydrophosphinylation of 1,3-dienes and phosphine oxides

Scheme 30. Pd-catalyzed asymmetric hydrophosphinylation of allenes and phosphine oxides

Scheme 31. Pd-catalyzed asymmetric hydrophosphinylation of methylenecyclopropanes and phosphine oxides

Scheme 32. Ni-catalyzed asymmetric hydrophosphinylation of 2-azadienes and phosphine oxides

Scheme 33. Pd-catalyzed asymmetric hydrophosphinylation of alkynes and phosphine oxides

Scheme 34. Synthesis of novel P-chiral monophosphorus ligands

Scheme 35. Pd-catalyzed asymmetric hydrophosphorylation of alkynes and phosphine oxides

Scheme 36. Ni-catalyzed asymmetric hydrophosphinylation of unactivated alkynes and phosphine oxides

Scheme 37. Ni-catalyzed asymmetric hydrophosphinylation of conjugated enynes and phosphine oxides

Scheme 38. Cu/CPA-catalyzed asymmetric hydrophosphinylation of alkynes and phosphine oxides

Scheme 39. Copper-catalyzed asymmetric hydrophosphinylation of α,β-unsaturated thioamides and phosphinothioates

Scheme 40. NHC-catalyzed asymmetric hydrophosphination of diarylphosphines and α-bromoenals

Scheme 41. Chiral bifunctional squaramide catalyzed asymmetric hydrophosphinylation of o-QMs methides and phosphine oxides

Scheme 42. Chiral bifunctional phosphonium salt catalyzed asymmetric hydrophosphinylation of p-QMs methides and phosphine oxides

Scheme 43. Chiral bifunctional thiourea catalyzed enantioselective hydrophosphinylation of sulfonyl indoles

Scheme 44. Chiral bifunctional diaminomethylenemalononitrile catalyzed asymmetric hydrophosphonylation of phosphine oxides and chalcones

Scheme 45. Chiral oxazaborolidines-catalyzed asymmetric hydrophosphinylation of α,β-unsaturated carbonyl compounds and phosphine oxides

Scheme 46. Proposed mechanism of chiral oxazaborolidines- catalyzed asymmetric hydrophosphinylation of α,β-unsaturated ketones

Scheme 47. Chiral Br?nsted base-catalyzed asymmetric hydrophosphinylation of 1-alkenylphosphine and phosphine oxides

Scheme 48. Chiral bis(guanidino)iminophosphorane catalyzed asymmetric hydrophosphinylation of 1,1-vinylazaheterocycle N-oxides and phosphine oxides

Scheme 49. Chiral Br?nsted acid-catalyzed asymmetric hydrophosphinylation of 2-vinylazaarenes and phosphine oxides

Scheme 50. Organocatalytic asymmetric hydrophosphinylation of nitroalkenes and phosphine sulfides

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