Chinese Journal of Organic Chemistry >
tert-Butyl Hydroperoxide-Mediated Synthesis of Phosphoroselenoates
Received date: 2021-07-25
Revised date: 2021-08-24
Online published: 2021-09-08
Supported by
Natural Science Foundation of Jiangsu Province(BK20170439); Science and Technology Plan Projects of Nantong City(JC2019102); Science and Technology Plan Projects of Nantong City(JC2020072)
Phosphoroselenoates have found widespread applications in the fields of organic synthesis and drug discovery. To this end, continuous efforts have been devoted to the development of novel and efficient methods for the synthesis of these compounds. A new method for the synthesis of phosphoroselenoates through oxidative coupling reaction of diselenides with phosphites by the utilization of t-butyl hydroperoxide (TBHP) as oxidant was herein developed. The distinct advantages of this protocol over all previous methods include mild reaction conditions, broad substrate scope, excellent yields, as well as transition metal- and base-free.
Key words: tert-butyl hydroperoxide; diselenide; phosphite; phosphoroselenoate
Yunqian Zhang , Chenfan Zhou , Gongqing Liu . tert-Butyl Hydroperoxide-Mediated Synthesis of Phosphoroselenoates[J]. Chinese Journal of Organic Chemistry, 2022 , 42(1) : 218 -225 . DOI: 10.6023/cjoc202107053
| [1] | (a) Carrasco, N.; Caton-Williams, J.; Brandt, G.; Wang, S.; Huang, Z. Angew. Chem., nt. Ed. 2006, 45, 94. |
| [1] | (b) Mitra, S.; Mukherjee, S.; Sen, S. K.; Hajra, A. Bioorg. Med. Chem. Lett. 2014, 24, 2198. |
| [1] | (c) Dinsdale, D.; Verschoyle, R. D. Biochem. Pharmacol. 2001, 61, 493. |
| [1] | (d) Mailahn, D. H.; Iarocz, L. E. B.; Nobre, P. C.; Perin, G.; Sinott, A.; Pesarico, A. P.; Birmann, P. T.; Savegnago, L.; Silva, M. S. Eur. J. Med. Chem. 2021, 213, 113052. |
| [2] | (a) Han, L.-B.; Choi, N.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 7000. |
| [2] | (b) Lopin, C.; Gouhier, G.; Gautier, A.; Piettre, S. R. J. Org. Chem. 2003, 68, 9916. |
| [2] | (c) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195. |
| [3] | Petragnani, N.; Toscano, V. G.; De Moura Campos, M. Chem. Ber. 1968, 101, 3070. |
| [4] | (a) Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7, 3100. |
| [4] | (b) Xu, Y.; Li, C.; Meng, J.; Huang, Y.; Fu, J.; Liu, B.; Liu, Y.; Chen, N. Chin. J. Org. Chem. 2021, 41, 1012. (in Chinese) |
| [4] | (许颖, 李晨, 孟建萍, 黄玉玲, 付纪源, 刘冰, 刘颖杰, 陈宁, 有机化学, 2021, 41, 1012.) |
| [5] | (a) Gao, Y.-X.; Tang, G.; Cao, Y.; Zhao, Y.-F. Synthesis 2009, 1081. |
| [5] | (b) Sun, K.; Wang, S.; Feng, R.; Zhang, Y.; Wang, X.; Zhang, Z.; Zhang, B. Org. Lett. 2019, 21, 2052. |
| [6] | (a) Zhang, X.; Shi, Z.; Shao, C.; Zhao, J.; Wang, D.; Zhang, G.; Li, L. Eur. J. Org. Chem. 2017, 1884. |
| [6] | (b) Li, Y.; Chen, S.; Su, L.; Li, J.; Xu, X. Chin. J. Org. Chem. 2013, 33, 1999. (in Chinese) |
| [6] | (李媛媛, 陈四海, 苏柳, 李建华, 许新华, 有机化学, 2013, 33, 1999.) |
| [6] | (c) Wang, J.; Wang, X.; Li, H.; Yan, J. J. Organomet. Chem. 2018, 859, 75. |
| [6] | (d) Chen, S.; Chen, J.; Xu, X.; He, Y.; Yi, R.; Qiu, R. J. Organomet. Chem. 2016, 818, 123. |
| [7] | (a) Choudhary, R.; Singh, P.; Bai, R.; Sharma, M. C.; Badsara, S. S. Org. Biomol. Chem. 2019, 17, 9757. |
| [7] | (b) Bhunia, S. K.; Das, P.; Jana, R. Org. Biomol. Chem. 2018, 16, 9243. |
| [7] | (c) Wang, X.; Wang, Q.; Xue, Y.; Sun, K.; Wu, L.; Zhang, B. Chem. Commun. 2020, 56, 4436. |
| [7] | (d) Wang, X.; Guo, S.; Zhang, Y.; Zhang, Z.; Zhang, G.; Ye, Y.; Sun, K. Adv. Synth. Catal. 2021, 363, 3290. |
| [8] | (a) Chen, D.-J.; Chen, Z.-C. J. Chem. Res. 2000, 370. |
| [8] | (b) Xu, Q.; Liang, C.-G.; Huang, X. Synth. Commun. 2003, 33, 2777. |
| [9] | (a) Guo, S.; Li, S.; Zhang, Z.; Yan, W.; Cai, H. Tetrahedron Lett. 2020, 61, 151566. |
| [9] | (b) Amri, N.; Wirth, T. Synlett 2020, 31, 1894. |
| [10] | Clive, D. L. J.; Menchen, S. M. J. Org. Chem. 1980, 45, 2347. |
| [11] | (a) Wang, P.-F.; Yi, W.; Ling, Y.; Ming, L.; Liu, G.-Q.; Zhao, Y. Chin. Chem. Lett. 2021, 32, 2587. |
| [11] | (b) Liu, G.-Q.; Yi, W.; Wang, P.-F.; Liu, J.; Ma, M.; Hao, D.-Y.; Ming, L.; Ling, Y. Green Chem. 2021, 23, 1840. |
| [11] | (c) Liang, Z.-P.; Yi, W.; Wang, P.-F.; Liu, G.-Q.; Ling, Y. J. Org. Chem. 2021, 86, 5292. |
| [12] | (a) Barnes, I.; Hjorth, J.; Mihalopoulos, N. Chem. Rev. 2006, 106, 940. |
| [12] | (b) Wu, X.-F.; Natte, K. Adv. Synth. Catal. 2016, 358, 336. |
| [13] | (a) Shi, M.; Wang, B.-Y.; Li, J. Eur. J. Org. Chem. 2005, 759. |
| [13] | (b) Perin, G.; Santoni, P.; Barcellos, A. M.; Nobre, P. C.; Jacob, R. G.; Lenardão, E. J.; Santi, C. Eur. J. Org. Chem. 2018, 1224. |
| [13] | (c) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Bartoli, D. Tetrahedron Lett. 1989, 30, 1417. |
| [13] | (d) Tiecco, M.; Testaferri, L.; Temperini, A.; Bagnoli, L.; Marini, F.; Santi, C. Synlett 2001, 1767. |
| [14] | Zhang, Q.-B.; Ban, Y.-L.; Yuan, P.-F.; Peng, S.-J.; Fang, J.-G.; Wu, L.-Z.; Liu, Q. Green Chem. 2017, 19, 5559. |
| [15] | (a) Gancarz, R. A.; Kice, J. L. Tetrahedron Lett. 1981, 22, 1661. |
| [15] | (b) Shimizu, M.; Takeda, R.; Kuwajima, I. Tetrahedron Lett. 1979, 419. |
| [16] | (a) Reich, H. J.; Willis, W., Jr.; Wollowitz, S. Tetrahedron Lett. 1982, 23, 3319. |
| [16] | (b) Kice, J. L.; McAfee, F.; Slebocka-Tilk, H. Tetrahedron Lett. 1982, 23, 3323. |
| [16] | (c) Kang, S. I.; Kice, J. L. J. Org. Chem. 1985, 50, 2968. |
| [17] | Singh, D.; Deobald, A. M.; Camargo, L. R. S.; Tabarelli, G.; Rodrigues, O. E. D.; Braga, A. L. Org. Lett. 2010, 12, 3288. |
| [18] | Loginova, E. I.; Nuretdinov, I. A.; Petrov, Y. A. Teor. Eksp. Khim. 1974, 10, 75. |
/
| 〈 |
|
〉 |