Chinese Journal of Organic Chemistry >
Fe(OTf)3-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure
Received date: 2023-01-18
Revised date: 2023-03-01
Online published: 2023-04-23
Supported by
National Natural Science Foundation of China(21772027)
A convenient approach acess to boronic ester containing N,O-acetal structure has been established through the Fe(OTf)3-catalyzed addition of N,O-acetal with organic boric acid. A series of N-O-acetal boronic ester compounds have been successfully prepared in 58%~98% yields. Moreover, these compounds retain the property of boronic ester and can be used for coupling reaction.
Key words: iminonium; N,O-acetal; boronic ester; addition reaction
Min Lü , Aimei Yang , Yu Zhang , Jianting Sun , Bangguo Wei . Fe(OTf)3-Catalyzed Synthesis of Boronic Ester Containing N,O-Acetal Structure[J]. Chinese Journal of Organic Chemistry, 2023 , 43(5) : 1777 -1785 . DOI: 10.6023/cjoc202301017
| [1] | (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. |
| [1] | (b) Matteson, D. S. J. Org. Chem. 2013, 78, 10009. |
| [1] | (c) Ranjani, G.; Nagarajan, R. Org. Lett. 2017, 19, 3974. |
| [1] | (d) Wang, A. E.; Huang, P. Q. Chin. J. Org. Chem. 2021, 41, 3738. (in Chinese) |
| [1] | (王爱娥, 黄培强, 有机化学, 2021, 41, 3738.) |
| [1] | (e) Mei, S. J.; Chen, Z. Chin. J. Org. Chem. 2021, 41, 2914. (in Chinese) |
| [1] | (吉梅山, 朱晨, 有机化学, 2021, 41, 2914.) |
| [1] | (f) Lu, H. X.; Li, B. J. Chin. J. Org. Chem. 2022, 42, 3167. (in Chinese) |
| [1] | (陆候祥, 李必杰, 有机化学, 2022, 42, 3167.) |
| [2] | (a) Paramore, A.; Frantz, S. Nat. Rev. Drug Discovery 2003, 2, 611. |
| [2] | (b) Sánchez-Serrano, I. Nat. Rev. Drug Discovery 2006, 5, 107. |
| [2] | (c) Sood, R.; Carloss, H.; Kerr, R.; Lopez, J.; Lee, M.; Druck, M.; Walters, I. B.; Noga, S. J. Am. J. Hematol. 2007, 84, 657. |
| [2] | (d) Mateos, M. V.; Oriol, A.; López, J. M.; Gutiérrez, N.; Teruel, A. I.; Paz, R.; Lara?a, J. G.; Bengoechea, E.; Martín, A.; Mediavilla, J. D.; Palomera, L.; Arriba, F.; González, Y.; Hernández, J. M.; Sureda, A.; Bello, J. L.; Bargay, J.; Pe?alver, F. J.; Ribera, J. M.; Mateos, M. L. M.; Sanz, R. G.; Cibeira, M. T.; Ramos, M. L. M.; Vidriales, M. B.; Paiva, B.; Montalbán, M. A.; Lahuerta, J. J.; Bladé, J.; Miguel, J. F. S. Lancet. Oncol. 2010, 11, 934. |
| [2] | (e) Robak, P.; Robak, T. Drugs R&D 2019, 19, 73. |
| [3] | (a) Shirley, M. Drugs 2016, 76, 405. |
| [3] | (b) Skorepova, E.; ?erňa, I.; Vlasáková, R.; Zvoní?ek, V.; Tkadlecová, M.; Du?ek, M. J. Mol. Struct. 2017, 1148, 22. |
| [3] | (c) Salvini, M.; Troia, R.; Giudice, D.; Pautasso, C.; Boccadoro, M.; Larocca, A. Expert. Opin. Drug Metab. Toxicol. 2018, 14, 91. |
| [4] | (a) Feng, Z.; Hellberg, M. Tetrahedron Lett. 2000, 41, 5813. |
| [4] | (b) Loewer, Y.; Weiss, C.; Biju, A. T.; Fr?hlich, R.; Glorius, F. J. Org. Chem. 2011, 76, 2324. |
| [4] | (c) Demetriades, M.; Leung, I. K. H.; Chowdhury, R.; Chan, M. C.; McDonough, M. A.; Yeoh, K. K..; Tian, Y. M.; Claridge, T. D. W.; Ratcliffe, P. J.; Woon, E. C. Y.; Schofield, C. J. Angew. Chem., Int. Ed. 2012, 51, 6672. |
| [4] | (d) McClary, C. A.; Taylor, M. S. Carbohyd. Res. 2013, 381, 112. |
| [4] | (e) Zhang, T.; Chen, X.; Xiao, C.; Zhuang, X.; Chen, X. Polym. Chem. 2017, 8, 6209. |
| [4] | (f) Gupta, A. K.; Yin, X.; Mukherjee, M.; Desai, A. A.; Mohammadlou, A.; Jurewicz, K.; Wulff, W. D. Angew. Chem., Int. Ed. 2019, 58, 3361. |
| [4] | (g) Chao, S.; Lv, X.; Ma, N.; Shen, Z.; Zhang, F.; Pei, Y.; Pei, Z. Chem. Commun. 2020, 56, 8861. |
| [4] | (h) Wang, L. J.; Sheng, X. L.; Wang, J.; Zhang, Y. H. Chin. J. Org. Chem. 2021, 41, 567. (in Chinese) |
| [4] | (王李娟, 盛显良, 王杰, 张玉辉, 有机化学, 2021, 41, 567.) |
| [5] | Robinson, L. L.; Self, J. L.; Fusi, A. D.; Bates, M. W.; Read De Alaniz, J.; Hawker, C. J.; Bates, C. M.; Sample, C. S. ACS Macro. Lett. 2021, 10, 857. |
| [6] | Lorand, J. P.; Edwards, J. O. J. Org. Chem. 1959, 24, 769. |
| [7] | Sugihara, J. M.; Bowman, C. M. J. Am. Chem. Soc. 1958, 80, 2443. |
| [8] | (a) Ferrier, R. J. Adv. Carbohydr. Chem. Biochem. 1978, 35, 31. |
| [8] | (b) Duggan, P. J.; Tyndalla, E. M. J. Chem. Soc., Perkin Trans. 1 2002, 1325. |
| [8] | (c) Roy, C. D.; Brown, H. C. J. Organomet. Chem. 2007, 692, 784. |
| [8] | (d) Meiland, M.; Heinze, T.; Guenther, W.; Liebert, T. Tetrahedron Lett. 2009, 50, 469. |
| [8] | (e) Spencer, J.; Baltus, C. B.; Patel, H.; Press, N. J.; Callear, S. K.; Male, L.; Coles, S. J. ACS Comb. Sci. 2011, 13, 24. |
| [8] | (f) Nishino, T.; Ohya, Y.; Murai, R.; Shirahata, T.; Yamamoto, D.; Makino, K.; Kaji, E. Heterocycles 2012, 84, 1123. |
| [8] | (g) Kaji, E.; Yamamoto, D.; Shirai, Y.; Ishige, K.; Arai, Y.; Shirahata, T.; Makino, K.; Nishino, T. Eur. J. Org. Chem. 2014, 2014, 3536. |
| [8] | (h) Nakagawa, A.; Tanaka, M.; Hanamura, S.; Takahashi, D.; Toshima, K. Angew. Chem., Int. Ed. 2015, 54, 10935. |
| [8] | (i) Kombala, C. J.; Ekanayake, D. I.; Gross, D. E. Tetrahedron Lett. 2017, 58, 3782. |
| [8] | (j) Shimada, N.; Urata, S.; Fukuhara, K.; Tsuneda, T.; Makino, K. Org. Lett. 2018, 20, 6064. |
| [8] | (k) Kilic, A.; Savci, A.; Alan, Y.; Beyazsakal, L. J. Organomet. Chem. 2020, 917, 121268. |
| [9] | (a) Liu, R. C.; Huang, W.; Ma, J. Y.; Wei, B. G.; Lin, G. Q. Tetrahedron Lett. 2009, 50, 4046. |
| [9] | (b) Feng, T.; Si, C. M.; Liu, R. C.; Fan, X.; Wei, B. G. Chin. J. Org. Chem. 2013, 33, 1291. (in Chinese) |
| [9] | (冯涛, 司长梅, 刘如成, 范翔, 魏邦国, 有机化学, 2013, 33, 1291.) |
| [9] | (c) Wang, X. M.; Liu, Y. W.; Wang, Q. E.; Zhou, Z.; Si, C. M.; Wei, B. G. Tetrahedron Lett. 2019, 75, 260. |
| [9] | (d) Chen, Z. D.; Chen, Z.; Wang, Q. E.; Si, C. M.; Wei, B. G. Tetrahedron Lett. 2020, 61, 152051. |
| [9] | (e) Zhang, Y. X.; Chen, L. Y.; Sun, J. T.; Si, C. M.; Wei, B. G. J. Org. Chem. 2020, 85, 12603. |
| [9] | (f) Han, X. L.; Nie, X. D.; Feng, Y. M.; Wei, B. G.; Si, C. M.; Lin, G. Q. Chin. Chem. Lett. 2021, 32, 3526. |
| [9] | (g) Sun, J. T.; Chen, L. Y.; Wei, B. G. Chin. J. Org. Chem. 2021, 41, 4320. (in Chinese) |
| [9] | (孙建婷, 陈玲艳, 魏邦国, 有机化学, 2021, 41, 4320.) |
| [9] | (h) Xu, W. K.; Guo, J. M.; Liu, C. H.; Sun, J. T.; Lv, M.; Wei, B. G. Org. Biomol. Chem. 2022, 20, 5086. |
| [10] | (a) Ciaravinol, E.; Coronadol, D.; Lanphear, C.; Hoberman, A.; Chanda, S. Int. J. Toxicol. 2016, 35, 530. |
| [10] | (b) Spergel, J. M.; Blaiss, M. S.; Lio, P.; Kessel, A.; Cantrell, W. C.; Takiya, L.; Werth, J. L.; O’Connell, M. A.; Zang, C.; Cork, M. J. Allergy Asthma Proc. 2021, 42, 425. |
| [10] | (c) Gupta, A. K.; Venkataraman, M.; Neil, H.; Shear, N. H.; Piguet, V. J. Dermatol. Treat. 2022, 33, 1213. |
| [10] | (d) Das, B. C.; Shareef, M. A.; Das, S.; Nandwana, N. K.; Das, Y.; Saito, M.; Weiss, L. M. Bioog. Med. Chem. 2022, 63, 116748. |
| [11] | (a) Dimitrijevic?, E.; Taylor, M. S. ACS Catal. 2013, 3, 945. |
| [11] | (b) Hall, D. G. Chem. Soc. Rev. 2019, 48, 3475. |
| [12] | Han, P.; Si, C. M.; Mao, Z. Y.; Li, H. T.; Wei, B. G.; Du, Z. T. Tetrahedron 2016, 72, 862. |
| [13] | (a) Liu, Y. W.; Ma, R. J.; Yan, J. H.; Zhou, Z.; Wei, B. G. Org. Biomol. Chem. 2018, 16, 771. |
| [13] | (b) Feng, Y. M.; Nie, X. D.; Sun, J. T.; Xu, W. K.; Wei, B. G. Org. Biomol. Chem. 2021, 19, 7883. |
| [14] | (a) Han, P.; Mao, Z. Y.; Si, C. M.; Zhou, Z.; Wei, B. G.; Lin, G. Q. J. Org. Chem. 2019, 84, 914. |
| [14] | (b) Wang, X. M.; Liu, Y. W.; Ma, R. J.; Si, C. M.; Wei, B. G. J. Org. Chem. 2019, 84, 11261. |
| [14] | (c) Han, X. L.; Nie, X. D.; Chen, Z. D.; Si, C. M.; Wei, B. G.; Lin, G. Q. J. Org. Chem. 2020, 85, 13567. |
| [14] | (d) Chen, Z. D.; Xu, W. K.; Guo, J. M.; Chen, L.; Wei, B. G.; Si, C. M.; Lin, G. Q. J. Org. Chem. 2021, 86, 11442. |
| [14] | (e) Sun, J. T.; Li, X.; Yang, T. Y.; Lv, M.; Chen, L. Y.; Wei, B. G. Org. Biomol. Chem. 2022, 20, 6571. |
| [14] | (f) Liu, C. H.; Guo, J. M.; Li, X.; Sun, J. T.; Wei, B. G.; Si, C. M. Chem. Commun. 2022, 58, 10841. |
| [15] | Wang, Q.; Tang, X. Y.; Shi, M. Angew. Chem., Int. Ed. 2016, 55, 10811. |
| [16] | (a) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513. |
| [16] | (b) Zhao, X. X.; Chang, H. H.; Li, X.; Wei, W. L. Chin. J. Org. Chem. 2015, 35, 1650. (in Chinese) |
| [16] | (赵晓霞, 常宏宏, 李兴, 魏文珑, 有机化学, 2015, 35, 1650.) |
| [16] | (c) Chatterjee, A.; Ward, T. R. Catal. Lett. 2016, 146, 820. |
| [16] | (d) Lou, T. S. B.; Michael, C.; Willis, M. C. Tetrahedron 2020, 76, 130782. |
| [16] | (e) Kassel, V. M.; Hanneman, C. M.; Delaney, C. P.; Denmark, S. E. J. Am. Chem. Soc. 2021, 143, 13845. |
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