Transition Metal-Catalyzed C—P Bond Activation

doi:10.6023/cjoc202105053

Abstract

Transition metal-catalyzed C—P bond activation provides an ecomomical and high-efficient route for the synthesis of organic phosphine compounds, and has received increasing attention in recent years. Owing to high bond energy of C—P bond and strong coordinative ability of P atom, the activation of C—P bond has been a fomidable challenge. Relying on substrate-preactivation and various catalysts, great progress has been achieved. This review will give a summary of this field, and according to different mechanisms of C—P bond activation and strategies of substrate pre-activation, a detailed description on reaction type, development, characteristics and mechanism will be made.

Key words: organophosphines, transition metal, C—P bond activation

Cite this article

Fengping Zhang, Yuxin Luan, Mengchun Ye. Transition Metal-Catalyzed C—P Bond Activation[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3880-3891.

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Fig. & Tab. 32

Figure 1. Ligand exchange between Pd and P

Figure 2. Proposed quaternary-phosphonium-salt key intermediate

Figure 3. Ring-opening reaction of 5-membered P-ring with arylpalladium

Figure 4. Ring-opening reaction of 5-membered P-ring with methylpalladium

Figure 5. Sulfonate-directed group exchange between Pd—Me and P—Ar

Figure 6. Decomposition pathways of BINAP

Figure 7. P-directed group exchange between Pd—Me and P—Ar

Figure 8. Bidentate group-enabled C—P bond activation

Figure 9. Palladium-catalyzed transformation of phosphonium salts

Figure 10. Competitive oxidative addition between P—Ph and Ar—Br bond

Figure 11. Palladium catalyzed intermolecular arylation

Figure 12. Nickel-catalyzed intermolecular arylation

Figure 13. Group exchange in Palladium-catalyzed Stille coupling reaction

Figure 14. Pd-catalyzed phosphination reaction of aryl halides with triarylphosphines

Figure 15. Pd-catalyzed intramolecular C—H phosphination

Figure 16. Pd-catalyzed intramolecular C—Br phosphination

Figure 17. Ar3P as arylating reagent in Pd-catalyzed Heck-type reaction

Figure 18. Pd-catalyzed phosophination of acylphosphine with PhI

Figure 19. Pd-catalyzed intramolecular phosphination

Figure 20. Ni-catalyzed intermolecular phosphination

Figure 21. Pd-catalyzed intramolecular arylphosphination

Figure 22. C—P bond activation via pyrazole direction

Figure 23. Pd-catalyzed decarbonylation-type C—P transformation

Figure 24. Ni-catalyzed decarbonylation-type C—P transformation

Figure 25. Pd-catalyzed decarbonylation-type C—P transformation

Figure 26. Strained ring-enabled C—P transformation

Figure 27. P atom-directed C—P bond activation

Figure 28. Bidentate group-enabled C—P bond activation

Figure 29. Catalyst-enabled C—P bond activation

Figure 30. NHC-Ni-enabled C—P bond activation

Figure 31. Transformation of C—P bond by addition-elimina- tion pathway of P=O bond

Figure 32. Transformation of C—P bond by addition-elimina- tion pathway of P—C(O) bond

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过渡金属催化的C—P键活化