Citation: Wen Jiang, Jieli Lin, Zhongshu Li. 低配位含磷官能团的研究进展[J]. University Chemistry, ;2025, 40(8): 138-151. doi: 10.12461/PKU.DXHX202409144 shu

低配位含磷官能团的研究进展

School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, China

Corresponding author: Zhongshu Li, lizhsh6@mail.sysu.edu.cn
Received Date: 30 September 2024
Revised Date: 26 December 2024

官能团是分子组成的重要构筑基元，决定着分子的物理化学性质。对官能团的结构、性质和功能的研究是合成化学最核心的内容，进而构筑了现代合成化学的理论体系。在“发现和创造新物质”这一化学学科核心工作中，设计和开发新型官能团尤为重要。随着合成技术的进步，逐渐出现了一些含P、B、S、Si等新型官能团的报道。基于对角线规则，含磷官能团可能会表现出类似含碳官能团的性质。同时，磷元素的引入还将进一步调节官能团的位阻和电子性质，从而展现出其独特的物理化学性质和应用潜力。本文综述了近年来低配位含磷官能团，如磷炔、双磷分子、磷宾、磷烯、双磷烯、磷杂苯等的研究进展，并对该领域未来的发展方向进行展望。
- Phosphorus-containing functional groups,
- Diagonal rule,
- Organophosphorus,
- Low-coordinated phosphorus
1. [1]
  Xu, G.; Senanayake, C. H.; Tang, W. Acc. Chem. Res. 2019, 52, 1101.
2. [2]
  Kutzelnigg, W. Angew. Chem. Int. Ed. Engl. 1984, 23, 272.
3. [3]
  Dillon, K. B.; Mathey, F.; Nixon, J. F. Phosphorus: The Carbon Copy: From Organophosphorus to Phospha-organic Chemistry; Wiley: West Sussex, UK, 1998.
4. [4]
  Mathey, F.; Duan, Z. Sci. Sin. Chim. 2010, 40, 888.
5. [5]
  Laurent, J. C. T. R. B.-S.; King, M. A.; Kroto, H. W.; Nixon, J. F.; Suffolk, R. J. J. Chem. Soc. Dalton Trans. 1983, 755.
6. [6]
  Bani-Fwaz, M. Z. J. Coord. Chem. 2020, 73, 887.
7. [7]
  Chirila, A.; Wolf, R.; Chris Slootweg, J.; Lammertsma, K. Coord. Chem. Rev. 2014, 270–271, 57.
8. [8]
  Gier, T. E. J. Am. Chem. Soc. 1961, 83, 1769.
9. [9]
  Hopkinson, M. J.; Kroto, H. W.; Nixon, J. F.; Simmons, N. P. C. J. Chem. Soc. Chem. Commun. 1976, 513.
10. [10]
  Regitz, M. Chem. Rev. 1990, 90, 191.
11. [11]
  Becker, G.; Gresser, G.; Uhl, W. Z. Naturforsch. B 1981, 36, 16.
12. [12]
  Markl, G.; Sejpka, H. Tetrahedron Lett. 1985, 26, 5507.
13. [13]
  Laurent, J. C. T. R. B. S.; Cooper, T. A.; Kroto, H. W.; Nixon, J. F.; Ohashi, O.; Ohno, K. J. Mol. Struct. 1982, 79, 215.
14. [14]
  Kroto, H. W.; Nixon, J. F.; Simmons, N. P. C. J. Mol. Spectrosc. 1980, 82, 185.
15. [15]
  Kroto, H. W.; Nixon, J. F.; Simmons, N. P. C. J. Mol. Spectrosc. 1979, 77, 270.
16. [16]
  Karaghiosoff, K.; Schmidpeter, A. Phosphorus, Sulfur Relat. Elem. 1988, 36, 217.
17. [17]
  Nixon, J. F. Chem. Rev. 1988, 88, 1327.
18. [18]
  Guillemin, J.-C.; Janati, T.; Denis, J.-M. J. Org. Chem. 2001, 66, 7864.
19. [19]
  Transue, W. J.; Yang, J.; Nava, M.; Sergeyev, I. V.; Barnum, T. J.; McCarthy, M. C.; Cummins, C. C. J. Am. Chem. Soc. 2018, 140, 17985.
20. [20]
  Benson, S. W. J. Chem. Educ. 1965, 42, 502.
21. [21]
  Bock, H.; Mueller, H. Inorg. Chem. 1984, 23, 4365.
22. [22]
  Piro, N. A.; Figueroa, J. S.; McKellar, J. T.; Cummins, C. C. Science 2006, 313, 1276.
23. [23]
  Velian, A.; Nava, M.; Temprado, M.; Zhou, Y.; Field, R. W.; Cummins, C. C. J. Am. Chem. Soc. 2014, 136, 13586.
24. [24]
  Eckhardt, A. K.; Riu, M.-L. Y.; Ye, M.; Müller, P.; Bistoni, G.; Cummins, C. C. Nat. Chem. 2022, 14, 928.
25. [25]
  Wang, S.; Sears, J. D.; Moore, C. E.; Rheingold, A. L.; Neidig, M. L.; Figueroa, J. S. Science 2022, 375, 1393.
26. [26]
  Xu, L. T.; Dunning, T. H. J. Chem. Theo. Comput. 2015, 11, 2496.
27. [27]
  Nesterov, V.; Reiter, D.; Bag, P.; Frisch, P.; Holzner, R.; Porzelt, A.; Inoue S. Chem. Rev. 2018, 118, 9678.
28. [28]
  Hirai, K.; Itoh, T.; Tomioka, H. Chem. Rev. 2009, 109, 3275.
29. [29]
  Iwamoto, E.; Hirai, K.; Tomioka, H. J. Am. Chem. Soc. 2003, 125, 14664.
30. [30]
  Tomioka, H.; Iwamoto, E.; Itakura H.; Hirai, K. Nature 2001, 412, 626.
31. [31]
  Benkő, Z.; Streubel, R.; Nyulászi, L. Dalton Trans. 2006, 4321.
32. [32]
  Li, X.; Lei, D.; Chiang, M. Y.; Gaspar, P. P. J. Am. Chem. Soc. 1992, 114, 8526.
33. [33]
  Li, X.; Weissman, S. I.; Lin, T.-S.; Gaspar, P. P.; Cowley, A. H.; Smirnov, A. I. J. Am. Chem. Soc. 1994, 116, 7899.
34. [34]
  Akimov, A. V.; Ganushevich, Y. S.; Korchagin, D. V.; Miluykov, V. A.; Misochko, E. Y. Angew. Chem. Int. Ed. 2017, 56, 7944.
35. [35]
  Nguyen, M. T.; Van Keer, A.; Vanquickenborne, L. G. J. Org. Chem. 1996, 61, 7077.
36. [36]
  Liu, L.; Ruiz, D. A.; Munz, D.; Bertrand, G. Chem 2016, 1, 147.
37. [37]
  Luo, Q.; Liu, T.; Huang, L.; Yang, C.; Lu, W. Angew. Chem. Int. Ed. 2024, 63, e202405122.
38. [38]
  Chen, Y.; Su, P.; Wang, D.; Ke, Z.; Tan, G. Nat. Commun. 2024, 15, 4579.
39. [39]
  Liu, L. L.; Zhou, J.; Andrews, R.; Stephan, D. W. J. Am. Chem. Soc. 2018, 140, 7466.
40. [40]
  Riu, M.-L. Y.; Eckhardt, A. K.; Cummins, C. C. J. Am. Chem. Soc. 2022, 144, 7578.
41. [41]
  Saint-Denis, T. G.; Wheeler, T. A.; Chen, Q.; Balázs, G.; Settineri, N. S.; Scheer, M.; Tilley, T. D. J. Am. Chem. Soc. 2024, 146, 4369.
42. [42]
  van Eis, M. J.; Zappey, H.; de Kanter, F. J. J.; de Wolf, W. H.; Lammertsma, K.; Bickelhaupt, F. J. Am. Chem. Soc. 2000, 122, 3386.
43. [43]
  Velian, A.; Cummins, C. C. J. Am. Chem. Soc. 201, 134, 13978.
44. [44]
  Schmidt, M. W.; Truong, P. N.; Gordon, M. S. J. Am. Chem. Soc. 1987, 109, 5217.
45. [45]
  Recker, G. Z. Anorg. Allg. Chem. 1976, 423, 242.
46. [46]
  Ziółkowska, A.; Doroszuk, J.; Ponikiewski, Ł. Organometallics 2023, 42, 505.
47. [47]
  Klebach, T. C.; Lourens, R.; Bickelhaupt, F. J. Am. Chem. Soc. 1978, 100, 4886.
48. [48]
  Hibbs, D. E.; Jones, C.; Richards, A. F. J. Chem. Soc. Dalton Trans. 1999, 3531.
49. [49]
  Romanenko, V.; Ruban, A.; Povolotskii, M.; Polyachenko, L.; Markovskii, L. Zh. Org. Khim. 1986, 56, 1186.
50. [50]
  Appel, R.; Immenkeppel, M. Z. Anorg. Allg. Chem. 1987, 553, 7.
51. [51]
  Yam, M.; Chong, J. H.; Tsang, C.-W.; Patrick, B. O.; Lam, A. E.; Gates, D. P. Inorg. Chem. 2006, 45, 5225.
52. [52]
  Shah, S.; Protasiewicz, J. D. Chem. Commun. 1998, 1585.
53. [53]
  Breen, T. L.; Stephan, D. W. J. Am. Chem. Soc. 1995, 117, 11914.
54. [54]
  Masuda, J. D.; Jantunen, K. C.; Ozerov, O. V.; Noonan, K. J. T.; Gates, D. P.; Scott, B. L.; Kiplinger, J. L. J. Am. Chem. Soc. 2008, 130, 2408.
55. [55]
  Lacombe, S.; Gonbeau, D.; Cabioch, J. L.; Pellerin, B.; Denis, J. M.; Pfister-Guillouzo, G. J. Am. Chem. Soc. 1988, 110, 6964.
56. [56]
  Weber, L. Eur. J. Inorg. Chem. 2000, 2000, 2425.
57. [57]
  Meriem, A.; Majoral, J.-P.; Revel, M.; Navech, J. Tetrahedron Lett. 1983, 24, 1975.
58. [58]
  Köhler, H.; Michaelis, A. Ber. Dtsch. Chem. Ges. 1877, 10, 807.
59. [59]
  Daly, J. J.; Maier, L. Nature 1964, 203, 1167.
60. [60]
  Daly, J. J.; Maier, L. Nature 1965, 208, 383.
61. [61]
  Yoshifuji, M.; Shima, I.; Inamoto, N.; Hirotsu, K.; Higuchi, T. J. Am. Chem. Soc. 1981, 103, 4587.
62. [62]
  Caminade, A.-M.; Verrier, M.; Ades, C.; Paillous, N.; Koenig, M. J. Chem. Soc. Chem. Commun. 1984, 875.
63. [63]
  Masaaki, Y.; Takahiro, S.; Naoki, I. Chem. Lett. 1988, 17, 1735.
64. [64]
  Asami, S.-S.; Okamoto, M.; Suzuki, K.; Yamashita, M. Angew. Chem. Int. Ed. 2016, 55, 12827.
65. [65]
  Smit, C. N.; van der Knaap, T. A.; Bickelhaupt, F. Tetrahedron Lett. 1983, 24, 2031.
66. [66]
  Liu, L. L.; Ruiz, D. A.; Dahcheh, F.; Bertrand, G.; Suter, R.; Tondreau, A. M.; Grützmacher, H. Chem. Sci. 2016, 7, 2335.
67. [67]
  Escudie, J.; Couret, C.; Ranaivonjatovo, H.; Satgé, J. J. Chem. Soc. Chem. Commun. 1984, 1621.
68. [68]
  Yoshifuji, M.; Shibayama, K.; Inamoto, N.; Matsushita, T.; Nishimoto, K. J. Am. Chem. Soc. 1983, 105, 2495.
69. [69]
  Doddi, A.; Bockfeld, D.; Zaretzke, M.-K.; Kleeberg, C.; Bannenberg, T.; Tamm, M. Dalton Trans. 2017, 46, 15859.
70. [70]
  Niecke, E.; Altmeyer, O.; Nieger, M. Angew. Chem. Int. Ed. 1991, 30, 1136.
71. [71]
  Romanenko, V. D.; Ruban, A. V.; Iksanova, S. V.; Polyachenko, L. K.; Markovski, L. N. Phosphorus, Sulfur Relat. Elem. 1985, 22, 365.
72. [72]
  Markovski, L. N.; Romanenko, V. D.; Ruban, A. V. Phosphorus, Sulfur Relat. Elem. 1987, 30, 447.
73. [73]
  Liu, L. L.; Cao, L. L.; Zhou, J.; Stephan, D. W. Angew. Chem. Int. Ed. 2019, 58, 273.
74. [74]
  Niecke, E.; Kramer, B.; Nieger, M. Angew. Chem. Int. Ed. 1989, 28, 215.
75. [75]
  Weber, L.; Ebeler, F.; Ghadwal, R. S. Coord. Chem. Rev. 2022, 461, 214499.
76. [76]
  Lin, J.; Liu, S.; Zhang, J.; Grützmacher, H.; Su, C.-Y.; Li, Z. Chem. Sci. 2023, 14, 10944.
77. [77]
  Weber, L. Chem. Rev. 1992, 92, 1839.
78. [78]
  Wong, T. C.; Bartell, L. S. J. Chem. Phys. 1974, 61, 2840.
79. [79]
  Baldridge, K. K.; Gordon, M. S. J. Am. Chem. Soc. 1988, 110, 4204.
80. [80]
  Nyulászi, L.; Keglevich, G. Heteroat. Chem. 1994, 5, 131.
81. [81]
  Zhang, J.; Li, Y.; Liu, S.; Lin, J.; Fan, Y.-N.; Li, Z. Eur. J. Inorg. Chem. 2023, 26, e202300595.
82. [82]
  Zhang, J.; Hou, Y.; Liu, S.; Lin, J.; Li, Z. Dalton Trans. 2024, 53, 5608.
83. [83]
  Hou, Y.; Li, Z.; Li, Y.; Liu, P.; Su, C.-Y.; Puschmann, F.; Grützmacher, H. Chem. Sci. 2019, 10, 3168.
84. [84]
  Chen, X.; Li, Z.; Grützmacher, H. Chem. Eur. J. 2018, 24, 8432.
85. [85]
  Müller, C.; Broeckx, L. E. E.; de Krom, I.; Weemers, J. J. M. Eur. J. Inorg. Chem. 2013, 2013, 187.
86. [86]
  Coles, N. T.; Sofie Abels, A.; Leitl, J.; Wolf, R.; Grützmacher, H.; Müller, C. Coord. Chem. Rev. 2021, 433, 213729.
87. [87]
  Müller, C.; Vogt, D. Phosphorus Compounds: Advanced Tools in Catalysis and Material Sciences; Peruzzini, M., Gonsalvi, L. Eds.; Springer: Dordrecht, Netherlands, 2011; p. 151.
88. [88]
  Müller, C.; Vogt, D. Dalton Trans. 2007, 5505.
89. [89]
  Märkl, G. Angew. Chem. Int. Ed. 1966, 5, 846.
90. [90]
  Carrasco, A. C.; Pidko, E. A.; Masdeu-Bultó, A. M.; Lutz, M.; Spek, A. L.; Vogt, D.; Müller, C. New J. Chem. 2010, 34, 1547.
91. [91]
  Müller, C.; Pidko, E. A.; Staring, A. J. P. M.; Lutz, M.; Spek, A. L.; van Santen, R. A.; Vogt, D. Chem. Eur. J. 2008, 14, 4899.
92. [92]
  Müller, C.; Pidko, E. A.; Totev, D.; Lutz, M.; Spek, A. L.; van Santen, R. A.; Vogt, D. Dalton Trans. 2007, 5372.
93. [93]
  Müller, C.; Pidko, E. A.; Lutz, M.; Spek, A. L.; Vogt, D. Chem. Eur. J. 2008, 14, 8803.
94. [94]
  Ashe, A. J. III. J. Am. Chem. Soc. 1971, 93, 3293.
95. [95]
  Mulliken, R. S. J. Am. Chem. Soc. 1950, 72, 4493.
96. [96]
  Rösch, W.; Regitz, M. Z. Naturforsch. B 1986, 41, 931.
97. [97]
  Chen, X.; Alidori, S.; Puschmann, F. F.; Santiso-Quinones, G.; Benkő, Z.; Li, Z.; Becker, G.; Grützmacher, H.-F.; Grützmacher, H. Angew. Chem. Int. Ed. 2014, 53, 1641.
98. [98]
  Avarvari, N.; Le Floch, P.; Mathey, F. J. Am. Chem. Soc. 1996, 118, 11978.
99. [99]
  Avarvari, N.; Le Floch, P.; Charrier, C.; Mathey, F. Heteroat. Chem. 1996, 7, 397.
100. [100]
  Nakajima, K.; Takata, S.; Sakata, K.; Nishibayashi, Y. Angew. Chem. Int. Ed. 2015, 54, 7597.
1. [1]
  Junyuan Zhang , Zhiwei Miao . 有机磷杀虫剂的前世今生. University Chemistry, 2025, 40(6): 129-138. doi: 10.12461/PKU.DXHX202408118
2. [2]
  Qilong Fang , Yiqi Li , Jiangyihui Sheng , Quan Yuan , Jie Tan . Magical Pesticide Residue Detection Test Strips: Aptamer-based Lateral Flow Test Strips for Organophosphorus Pesticide Detection. University Chemistry, 2024, 39(5): 80-89. doi: 10.3866/PKU.DXHX202310004
3. [3]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
4. [4]
  Jing Wang , Pingping Li , Yuehui Wang , Yifan Xiu , Bingqian Zhang , Shuwen Wang , Hongtao Gao . Treatment and Discharge Evaluation of Phosphorus-Containing Wastewater. University Chemistry, 2024, 39(5): 52-62. doi: 10.3866/PKU.DXHX202309097
5. [5]
  Ruilan Fan , Xiaoling Huang . 磷源的选择及三种含磷阻燃剂的合成与阻燃性. University Chemistry, 2025, 40(8): 181-191. doi: 10.12461/PKU.DXHX202410025
6. [6]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
7. [7]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
8. [8]
  Linfeng Zhou , Yulin Zhang , Suhao Lin , Longguan Zhu . 2023年北京大学金秋营及第37届中国化学奥林匹克决赛磷团簇相关试题解析与拓展. University Chemistry, 2025, 40(8): 376-387. doi: 10.12461/PKU.DXHX202411030
9. [9]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
10. [10]
  Fengxiao Wang , Zhiwei Miao , Yaofeng Yuan . 有机磷化学与化学教学. University Chemistry, 2025, 40(8): 158-168. doi: 10.12461/PKU.DXHX202410077
11. [11]
  Wenke ZHENG , Ce LIU , Wei CHEN , Hongshan KE , Fanlong ZENG , Yibo LEI , Anyang LI , Wenyuan WANG . Synthesis and bonding analysis of low-coordinate Fe and Cr complexes with ultra-bulky silylamino groups. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1285-1293. doi: 10.11862/CJIC.20250095
12. [12]
  Shuai Yuan , Yaofeng Yuan . Academician Chengye Yuan and Organic Phosphorus Chemistry. University Chemistry, 2025, 40(7): 393-400. doi: 10.12461/PKU.DXHX202409123
13. [13]
  Caiyun Jin , Zexuan Wu , Guopeng Li , Zhan Luo , Nian-Wu Li . Phosphazene-based flame-retardant artificial interphase layer for lithium metal batteries. Acta Physico-Chimica Sinica, 2025, 41(8): 100094-0. doi: 10.1016/j.actphy.2025.100094
14. [14]
  Jia Wang , Qing Qin , Zhe Wang , Xuhao Zhao , Yunfei Chen , Liqiang Hou , Shangguo Liu , Xien Liu . P-Doped Carbon-Supported Zn_xP_yO_z for Efficient Ammonia Electrosynthesis under Ambient Conditions. Acta Physico-Chimica Sinica, 2024, 40(3): 2304044-0. doi: 10.3866/PKU.WHXB202304044
15. [15]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
16. [16]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
17. [17]
  Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
18. [18]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
19. [19]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
20. [20]
  Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(11)
HTML views(4)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142