过渡金属催化的C—P键活化

doi:10.6023/cjoc202105053

摘要/Abstract

过渡金属催化的C—P键活化转化为有机膦化合物的合成提供了一条经济、高效的途径, 近年来受到了越来越多的关注. 然而由于C—P键较高的键能和P原子强的配位性能, C—P键活化一直较为挑战. 采用不同的底物预活化方法和各类催化剂, 过渡金属催化的C—P键活化转化已经取得了显著的进展. 本综述将对该领域的发展进行总结, 按照反应机理和底物预活化策略的不同, 分类阐述这些反应的类型, 发展、特点和机理等.

关键词: 有机膦化合物, 过渡金属催化, C—P键活化

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

引用此文

张凤萍, 栾玉新, 叶萌春. 过渡金属催化的C—P键活化[J]. 有机化学, 2021, 41(10): 3880-3891.

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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图/表 32

图1. Pd—P之间的配体交换现象

Figure 1. Ligand exchange between Pd and P

图2. 季鏻盐关键中间体的提出

Figure 2. Proposed quaternary-phosphonium-salt key intermediate

图3. 四元磷环和芳基钯的开环反应

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

图4. 五元膦环和甲基钯的开环反应

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

图5. 磺酸基导向的Pd—Me与P—Ar基团交换

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

图6. BINAP的分解途径

Figure 6. Decomposition pathways of BINAP

图7. P导向的Pd—Me与P—Ar基团交换

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

图8. 双齿导向基促进的C—P键活化

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

图9. 钯催化的季鏻盐转化

Figure 9. Palladium-catalyzed transformation of phosphonium salts

图10. 季鏻盐Ph—P和Ar—Br键的竞争性氧化加成

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

图11. 钯催化分子间芳基化反应

Figure 11. Palladium catalyzed intermolecular arylation

图12. 镍催化的分子间芳基化

Figure 12. Nickel-catalyzed intermolecular arylation

图13. 钯催化Stille偶联反应中的基团交换

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

图14. 钯催化卤代芳烃和三芳基膦的膦化反应

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

图15. 钯催化分子内C—H膦化反应

Figure 15. Pd-catalyzed intramolecular C—H phosphination

图16. 钯催化分子内C—Br膦化反应

Figure 16. Pd-catalyzed intramolecular C—Br phosphination

图17. 三芳基膦作为钯催化Heck型反应的芳基化试剂

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

图18. 钯催化酰基膦和PhI的膦化反应

Figure 18. Pd-catalyzed phosophination of acylphosphine with PhI

图19. 钯催化分子内膦化反应

Figure 19. Pd-catalyzed intramolecular phosphination

图20. 镍催化的分子分子间膦化反应

Figure 20. Ni-catalyzed intermolecular phosphination

图21. 钯催化炔烃分子内芳膦化反应

Figure 21. Pd-catalyzed intramolecular arylphosphination

图22. 吡唑导向的C—P键活化转化

Figure 22. C—P bond activation via pyrazole direction

图23. 钯催化脱羰型C—P键活化转化

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

图24. 镍催化脱羰型C—P键活化转化

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

图25. 钯催化脱羰型C—P键活化转化

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

图26. 张力环促进的C—P键活化转化

Figure 26. Strained ring-enabled C—P transformation

图27. P原子导向的C—P键活化

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

图28. 双齿导向基促进的C—P键活化

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

图29. 催化剂促进的C—P键的活化

Figure 29. Catalyst-enabled C—P bond activation

图30. NHC-Ni催化剂促进的C—P键的活化

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

图31. 通过P=O加成消去途径实现的C—P键的转化

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

图32. 通过P—C(O)加成消去途径实现的C—P键的转化

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

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