Research Progress in the Preparation of Aryl and Alkyl Mixed Phosphates

doi:10.6023/cjoc202105056

Abstract

Aryl and alkyl mixed phosphates are very important phosphorus containing organic compounds, which are widely used in many fields, such as biology, medicine, pesticide, polymer, and material science. The unique physical, chemical, and biological properties of phosphorus-based motifs provide more possibilities for their structural modification, derivatization, and potential application. Therefore, the research on the preparation of these compounds has important theoretical and practical significance. In this paper, the research progress of the synthesis methodologies of aryl and alkyl mixed phosphate in the past few decades is reviewed. The application examples are listed. The experimental methods and development process of the conversion of various kinds of phosphorus containing reagents to target compounds are summarized. The characteristics, mechanism, and application of the reaction are discussed selectively as well. We hope that this review can provide a reference for the development of new preparation protocols of mixed phosphate, and provide some useful references for scholars, graduate students, and others in the related fields.

Key words: synthetic method, mixed phosphate, organic phosphorus compound

Cite this article

Linyu Jiao, Hua Yu, Zihui Ning, Zhuo Li. Research Progress in the Preparation of Aryl and Alkyl Mixed Phosphates[J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4180-4191.

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Fig. & Tab. 44

Figure 1. Application of aryl and alkyl mixed phosphates in agriculture

Figure 2. Aryl and alkyl mixed phosphates as lipid prodrug

Figure 3. Application of aryl and alkyl mixed phosphates in biomedicine

Figure 4. Application of aryl and alkyl mixed phosphates in flame retardant

Figure 5. Mixed phosphates as fluorosurfactant

Scheme 1. Classical Atherton-Todd reaction formula

Scheme 2. Phosphorylation of flavonoids

Scheme 3. [3,3]-σ migratory rearrangement to prepare mixed phosphates

Scheme 4. Preparation of phosphate through Atherton-Todd reaction catalyzed by CuCl2

Scheme 5. One-pot synthesis of mixed phosphate under TCICA

Scheme 6. Synthesis of aryl and alkyl mixed phosphates catalyzed by LiI/TBHP

Scheme 7. Pyridine promoted esterification of phosphoryl chloride and ethanol

Scheme 8. Pyridine promoted esterification of diphenylphosphoryl chloride and tetrahydrofurfuryl alcohol

Scheme 9. Catalytic mechanism of titanium-based Lewis acid in the synthesis of mixed phosphates

Scheme 10. Reaction mechanism of MoOCl4 catalyzed synthesis of mixed phosphates

Scheme 11. Synthesis of cellulose diphenyl phosphate in ionic liquid

Scheme 12. Application of catalysts based on polyethylene glycol chains in the synthesis of mixed phosphates

Scheme 13. Triazene combined with polymer catalyzed P(O)—OH synthesis of mixed phosphatess

Scheme 14. Esterification of P(O)—OH compound catalyzed by SiO2—Cl

Scheme 15. p-TsOH-celite catalyzed esterification reaction with P(O)—OH compound

Scheme 16. Synthesis of mixed phosphates by “one-pot reaction” with the promotion of PPh3 and trichloroacetonitrile

Scheme 17. Alkali-promoted reaction of diphenylphosphoric acid with benzyl bromide to prepare mixed phosphates

Scheme 18. Esterification of P(O)—OH with aliphatic alcohols and diaryliodonium salts

Scheme 19. Preparation of mixed phosphates by oxidation and decomposition of phosphite

Scheme 20. Catalytic preparation of light-induced aryl and alkyl mixed phosphates

Scheme 21. Alcoholysis of triaryl phosphate under the action of zinc complex

Scheme 22. Alcoholysis of triaryl phosphate catalyzed by aluminum porphyrin dimer

Scheme 23. Hydrolysis and alcoholysis of triaryl phosphate catalyzed by UIO-66

Scheme 24. Tf2O/pyridine promoted continuous transesterification reaction

Scheme 25. Transesterification of triethyl phosphate promoted by P2O5

Scheme 26. Catalytic conversion of diphenyl azide phosphate and fatty alcohol under the action of copper

Scheme 27. Catalytic conversion of diphenyl azide phosphate and aliphatic alcohol under the action of zinc

Scheme 28. Catalytic conversion of diphenyl azide phosphate in heterogeneous system

Scheme 29. Application of phosphorylpyridinium salt intermediate in the synthesis of mixed phosphates

Scheme 30. Application of phosphorylpyridinium salt in the synthesis of mixed phosphates under the condition of high pressure mercury lamp

Scheme 31. Application of NCT-based new phosphorylation reagents in the synthesis of mixed phosphates

Scheme 32. Preparation of phosphoramide compounds from NCT and phosphoryl chloride

Scheme 33. Synthesis of novel phosphorylation reagents from oxazolidinone and phosphoryl chloride

Scheme 34. Application of new phosphorylation reagents containing oxazolidinone in the synthesis of phosphates

Scheme 35. Catalytic conversion of a novel phosphorylation reagent containing oxazolidinone under the action of copper salt

Scheme 36. Conversion scheme of benzotriazole phosphorylation reagent

Scheme 37. Application of benzotriazole phosphorylation reagents in the synthesis of mixed phosphates

Scheme 38. Synthetic route of DEPC

Scheme 39. Esterification reaction of diethyl cyanophosphonate with p-chlorophenol

References 64

[1]	Kozak, W.; Rachon, J.; Daśko, M.; Demkowicz, S. Asian J. Org. Chem. 2018, 7, 314. doi: 10.1002/ajoc.v7.2
[2]	Desloges, W.; Neverov, A. A.; Brown, R. S. Inorg. Chem. 2004, 43, 6752. pmid: 15476375
[3]	Timperley, C. M.; Casey, K. E.; Notman, S.; Sellers, D. J.; Williams, N. E.; Williams, N. H.; Williams, G. R. J. Fluorine Chem. 2006, 127, 1554. doi: 10.1016/j.jfluchem.2006.07.017
[4]	Selikhov, A. N.; Malysheva, Y. B.; Nyuchev, A. V.; Sitnikov, N. S.; Sharonova, E. A.; Shavyrin, A. S.; Combes, S.; Fedorov, A. Y. Russ. Chem. Bull. 2011, 60, 2003. doi: 10.1007/s11172-011-0304-7
[5]	Mills, S. J.; Dozol, H.; Vandeput, F.; Backers, K.; Woodman, T.; Erneux, C.; Spiess, B.; Potter, B. V. L. ChemBioChem 2006, 7, 1696. doi: 10.1002/cbic.v7:11
[6]	Silverberg, L. J.; Dillon, J. L.; Vemishetti, P. Tetrahedron Lett. 1996, 37, 771. doi: 10.1016/0040-4039(95)02294-5
[7]	Jiao, L.-Y.; Zhang, Z.; Yin, X.-M.; Li, Z.; Ma, X.-X. J. Catal. 2019, 379, 39. doi: 10.1016/j.jcat.2019.09.014
[8]	Shen, J.; Zhang, Y.; Yu, N.; Crump, D.; Li, J.; Su, H.; Letcher, R. J.; Su, G. Environ. Sci. Technol. 2019, 53, 2151. doi: 10.1021/acs.est.8b06246
[9]	Xu, D. CN 103360606, 2013.
[10]	Liu, W. CN 109912646, 2021.
[11]	Liang, R. CN 105833790, 2020.
[12]	Stubbings, W. A.; Riddell, N.; Chittim, B.; Venier, M. Environ. Sci. Technol. Lett. 2017, 4, 292. doi: 10.1021/acs.estlett.7b00195
[13]	Atherton, F. R.; Openshaw, H. T.; Todd, A. R. J. Chem. Soc. 1945, 660.
[14]	Atherton, F. R.; Todd, A. R. J. Chem. Soc. 1947, 674.
[15]	Cao, S.; Zhao, Y. Sci. China Chem. 2015, 45, 283. (in Chinese)
	(曹书霞, 赵玉芬, 中国科学, 化学, 2015, 45, 283.)
[16]	Le Corre, S. S.; Berchel, M.; Couthon-Gourvès, H.; Haelters, J.-P.; Jaffrès, P.-A. Beilstein J. Org. Chem. 2014, 10, 1166. doi: 10.3762/bjoc.10.117
[17]	Chen, X.; Yu, Y.; Qu, L.; Liao, X.; Zhao, Y. Synth. Commun. 2004, 34, 493. doi: 10.1081/SCC-120027289
[18]	Yang, Y.; Qu, C.; Chen, X.; Sun, K.; Qu, L.; Bi, W.; Hu, H.; Li, R.; Jing, C.; Wei, D.; Wei, S.; Sun, Y.; Liu, H.; Zhao, Y. Org. Lett. 2017, 19, 5864. doi: 10.1021/acs.orglett.7b02852
[19]	Okamoto, Y.; Kusano, T.; Takamuku, S. Bull. Chem. Soc. Jpn. 1988, 61, 3359. doi: 10.1246/bcsj.61.3359
[20]	Gupta, A. K.; Acharya, J.; Dubey, D. K.; Kaushik, M. P. Synth. Commun. 2007, 37, 3403. doi: 10.1080/00397910701483662
[21]	Anitha, T.; Ashalu, K. C.; Sandeep, M.; Mohd, A.; Wencel-Delord, J.; Colobert, F.; Reddy, K. R. Eur. J. Org. Chem. 2019, 7463.
[22]	Wu, J.; Wang, B. Zhejian Chem. Ind. 2008, 39, 27. (in Chinese)
	(吴晶, 王博, 浙江化工, 2008, 39, 27.)
[23]	Dhawan, B.; Redmore, D. J. Org. Chem. 1986, 51, 179. doi: 10.1021/jo00352a010
[24]	Powles, N.; Atherton, J.; Page, M. I. Org. Biomol. Chem. 2012, 10, 5940. doi: 10.1039/c2ob07130d
[25]	Jones, S.; Selitsianos, D. Org. Lett. 2002, 4, 3671. doi: 10.1021/ol026618q
[26]	Jones, S.; Selitsianos, D.; Thompson, K. J.; Toms, S. M. J. Org. Chem. 2003, 68, 5211. doi: 10.1021/jo034331g
[27]	Acharya, J.; Shakya, P. D.; Pardasani, D.; Palit, M.; Dubey, D. K.; Gupta, A. K. J. Chem. Res. 2005, 194.
[28]	Liu, C.-Y.; Pawar, V. D.; Kao, J.-Q.; Chen, C.-T. Adv. Synth. Catal. 2010, 352, 188. doi: 10.1002/adsc.v352:1
[29]	Xiao, P.; Zhang, J.; Feng, Y.; Wu, J.; He, J.; Zhang, J. Cellulose 2014, 21, 2369. doi: 10.1007/s10570-014-0256-9
[30]	Weiss-Shtofman, M.; Kramer, M.; Dobrovetsky, R.; Portno, M. Org. Lett. 2020, 22, 3722. doi: 10.1021/acs.orglett.0c01226
[31]	Vignola, N.; Dahmen, S.; Enders, D.; Bräse, S. J. Comb. Chem. 2003, 5, 138. pmid: 12625703
[32]	Sathe, M.; Gupta, A. K.; Kaushik, M. P. Tetrahedron Lett. 2006, 47, 3107. doi: 10.1016/j.tetlet.2006.02.159
[33]	Gupta, A. K.; Kumar, R.; Dubey, D. K.; Kaushik, M. P. J. Chem. Res. 2007, 328.
[34]	Kasemsuknimit, A.; Satyender, A.; Chavasiri, W.; Jang, D. O. Bull. Korean Chem. Soc. 2011, 32, 3486. doi: 10.5012/bkcs.2011.32.9.3486
[35]	Xiong, B.; Ye, Q.; Feng, X.; Zhu, L.; Chen, T.; Zhou, Y.; Au, C.-T.; Yin, S.-F. Tetrahedron. 2014, 70, 9057. doi: 10.1016/j.tet.2014.10.013
[36]	(a) Xiong, B.; Feng, X.; Zhu, L.; Chen, T.; Zhou, Y.; Au, C.-T.; Yin, S.-F. ACS Catal. 2015, 5, 537. doi: 10.1021/cs501523g
	(b) Xiong, B.; Zeng, K.; Zhang, S.; Zhou, Y.; Au, C.-T.; Yin, S.-F. Tetrahedron 2015, 71, 9293. doi: 10.1016/j.tet.2015.10.028
[37]	Xiong, B.; Cheng, Q.; Hu, C.; Zhang, P.; Liu, Y.; Tang, K. ChemistrySelect 2017, 2, 6891. doi: 10.1002/slct.201700716
[38]	Xiong, B.; Hu, C.; Li, H.; Zhou, C.; Zhang, P.; Liu, Y.; Tang, K. Tetrahedron Lett. 2017, 58, 2482. doi: 10.1016/j.tetlet.2017.05.036
[39]	Xiong, B.; Hu, C.; Gu, J.; Yang, C.; Zhang, P.; Liu, Y.; Tang, K. ChemistrySelect 2017, 2, 3376. doi: 10.1002/slct.201700596
[40]	Xiong, B.; Wang, G.; Zhou, C.; Liu, Y.; Li, J.; Zhang, P.; Tang, K. Phosphorus, Sulfur Silicon Relat. Elem. 2018, 193, 239. doi: 10.1080/10426507.2017.1395438
[41]	Bartlett, P. D.; Lonzetta, C. M.; J. Am. Chem. Soc. 1983, 105, 1984. doi: 10.1021/ja00345a054
[42]	Stephenson, L. M.; McClure, D. E. J. Am. Chem. Soc. 1973, 95, 3074. doi: 10.1021/ja00790a088
[43]	Oba, M.; Okada, Y.; Nishiyama, K.; Ando, W. Org. Lett. 2009, 11, 1879. doi: 10.1021/ol900240s
[44]	Tamilselvi, A.; Mugesh, G. Chem.-Eur. J. 2010, 16, 8878. doi: 10.1002/chem.201000282 pmid: 20575118
[45]	Kang, B.; Kurutz, J. W.; Youm, K.-T.; Totten, R. K.; Hupp, J. T.; Nguyen, S. T. Chem. Sci. 2012, 3, 1938. doi: 10.1039/c2sc00950a
[46]	Totten, R. K.; Ryan, P.; Kang, B.; Lee, S. J.; Broadbelt, L. J.; Snurr, R. Q.; Hupp, J. T.; Nguyen, S. T. Chem. Commun. 2012, 48, 4178. doi: 10.1039/c2cc17568a
[47]	Katz, M. J.; Mondloch, J. E.; Totten, R. K.; Park, J. K.; Nguyen, S. T.; Farha, O. K.; Hupp, J. T. Angew. Chem. Int. Ed. 2014, 53, 497. doi: 10.1002/anie.v53.2
[48]	Huang, H.; Ash, J.; Kang, J. Y. Org. Lett. 2018, 20, 4938. doi: 10.1021/acs.orglett.8b02073 pmid: 30088775
[49]	Nilsson, J.; Kraszewski, A.; Stawinski, J. J. Chem. Soc., erkin Trans. 2001, 2263.
[50]	Kaboudin, B.; Mostafalu, R. Phosphorus, Sulfur Silicon Relat. Elem. 2012, 187, 776. doi: 10.1080/10426507.2011.639822
[51]	Keith, J. M. J. Org. Chem. 2006, 71, 9540. pmid: 17137393
[52]	Kim, H.; Park, J.; Kim, J. G.; Chang, S. Org. Lett. 2014, 16, 5466. doi: 10.1021/ol502722j
[53]	Yamada, K.; Yamashita, M.; Sumiyoshi, T.; Nishimura, K.; Tomioka, K. Org. Lett. 2009, 11, 1631. doi: 10.1021/ol9003564
[54]	Haberhauer, G.; Rominger, F. Eur. J. Org. Chem. 2003, 3209.
[55]	Ying, J.; Gao, Q.; Wu, X.-F. Chem. Asian J. 2020, 15, 1540. doi: 10.1002/asia.v15.10
[56]	Jiao, L.-Y.; Zhang, Z.; Hong, Q.; Ning, Z.-H.; Liu, S.; Sun, M.; Hao, Q.; Xu, L.; Li, Z.; Ma, X.-X. Mol. Catal. 2020, 494, 111120.
[57]	Matsumoto, S.; Masuda, H.; Iwata, K.; Mitsunobu, O. Tetrahedron Lett. 1973, 14, 1733. doi: 10.1016/S0040-4039(01)96040-X
[58]	Maezaki, N.; Furusawa, A.; Hirose, Y.; Uchida, S.; Tanaka, T. Tetrahedron 2002, 58, 3493. doi: 10.1016/S0040-4020(02)00312-5
[59]	Jones, S.; Smanmoo, C. Tetrahedron Lett. 2004, 45, 1585. doi: 10.1016/j.tetlet.2004.01.003
[60]	Jones, S.; Smanmoo, C. Org. Lett. 2005, 7, 3271. doi: 10.1021/ol051104n
[61]	Panmand, D. S.; Tiwari, A. D.; Panda, S. S.; Monbaliu, J.-C. M.; Beagle, L. K.; Asiri, A. M.; Stevens, C. V.; Steel, P. J.; Hall, C. D.; Katritzky, A. R. Tetrahedron Lett. 2014, 55, 5898. doi: 10.1016/j.tetlet.2014.07.057
[62]	Harusawa, S.; Shioiri, T. Tetrahedron. 2016, 72, 8125. doi: 10.1016/j.tet.2016.09.070
[63]	Łopusiński, A. Heteroat. Chem. 2004, 15, 395. doi: 10.1002/(ISSN)1098-1071
[64]	Guzmán, A.; Diaz, E. Synth. Commun. 1997, 27, 3035. doi: 10.1080/00397919708005008

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