tert-Butyl Hydroperoxide-Mediated Synthesis of Phosphoroselenoates

doi:10.6023/cjoc202107053

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 218-225.DOI: 10.6023/cjoc202107053 Previous Articles Next Articles

ARTICLES

叔丁基过氧化氢介导的磷酸硒酯合成

张云倩, 周晨凡, 刘功清^*()

南通大学药学院南通 226001

收稿日期:2021-07-25 修回日期:2021-08-24 发布日期:2021-09-08
通讯作者: 刘功清
基金资助:
江苏省自然科学基金(BK20170439); 南通市科技(JC2019102); 南通市科技(JC2020072)

tert-Butyl Hydroperoxide-Mediated Synthesis of Phosphoroselenoates

Yunqian Zhang, Chenfan Zhou, Gongqing Liu()

School of Pharmacy, Nantong University, Nantong 226001

Received:2021-07-25 Revised:2021-08-24 Published:2021-09-08
Contact: Gongqing Liu
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)

1. .pdf(2581KB)

Abstract

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

Cite this article

Yunqian Zhang, Chenfan Zhou, Gongqing Liu. tert-Butyl Hydroperoxide-Mediated Synthesis of Phosphoroselenoates[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 218-225.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

References 18

[1]	(a) Carrasco, N.; Caton-Williams, J.; Brandt, G.; Wang, S.; Huang, Z. Angew. Chem., nt. Ed. 2006, 45, 94. pmid: 11226384
	(b) Mitra, S.; Mukherjee, S.; Sen, S. K.; Hajra, A. Bioorg. Med. Chem. Lett. 2014, 24, 2198. doi: 10.1016/j.bmcl.2014.03.008 pmid: 11226384
	(c) Dinsdale, D.; Verschoyle, R. D. Biochem. Pharmacol. 2001, 61, 493. pmid: 11226384
	(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. doi: 10.1016/j.ejmech.2020.113052 pmid: 11226384
[2]	(a) Han, L.-B.; Choi, N.; Tanaka, M. J. Am. Chem. Soc. 1996, 118, 7000. doi: 10.1021/ja9608860
	(b) Lopin, C.; Gouhier, G.; Gautier, A.; Piettre, S. R. J. Org. Chem. 2003, 68, 9916. doi: 10.1021/jo0348064
	(c) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. Tetrahedron Lett. 2000, 41, 10195. doi: 10.1016/S0040-4039(00)01830-X
[3]	Petragnani, N.; Toscano, V. G.; De Moura Campos, M. Chem. Ber. 1968, 101, 3070. doi: 10.1002/cber.v101:9
[4]	(a) Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7, 3100. doi: 10.1039/D0QO00849D
	(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) doi: 10.6023/cjoc202008009
	(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.) doi: 10.6023/cjoc202008009
[5]	(a) Gao, Y.-X.; Tang, G.; Cao, Y.; Zhao, Y.-F. Synthesis 2009, 1081.
	(b) Sun, K.; Wang, S.; Feng, R.; Zhang, Y.; Wang, X.; Zhang, Z.; Zhang, B. Org. Lett. 2019, 21, 2052. doi: 10.1021/acs.orglett.9b00240
[6]	(a) Zhang, X.; Shi, Z.; Shao, C.; Zhao, J.; Wang, D.; Zhang, G.; Li, L. Eur. J. Org. Chem. 2017, 1884.
	(b) Li, Y.; Chen, S.; Su, L.; Li, J.; Xu, X. Chin. J. Org. Chem. 2013, 33, 1999. (in Chinese)
	(李媛媛, 陈四海, 苏柳, 李建华, 许新华, 有机化学, 2013, 33, 1999.) doi: 10.6023/cjoc201304024
	(c) Wang, J.; Wang, X.; Li, H.; Yan, J. J. Organomet. Chem. 2018, 859, 75. doi: 10.1016/j.jorganchem.2018.01.057
	(d) Chen, S.; Chen, J.; Xu, X.; He, Y.; Yi, R.; Qiu, R. J. Organomet. Chem. 2016, 818, 123. doi: 10.1016/j.jorganchem.2016.06.010
[7]	(a) Choudhary, R.; Singh, P.; Bai, R.; Sharma, M. C.; Badsara, S. S. Org. Biomol. Chem. 2019, 17, 9757. doi: 10.1039/c9ob01921a pmid: 30483684
	(b) Bhunia, S. K.; Das, P.; Jana, R. Org. Biomol. Chem. 2018, 16, 9243. doi: 10.1039/c8ob02792g pmid: 30483684
	(c) Wang, X.; Wang, Q.; Xue, Y.; Sun, K.; Wu, L.; Zhang, B. Chem. Commun. 2020, 56, 4436. doi: 10.1039/D0CC01079K pmid: 30483684
	(d) Wang, X.; Guo, S.; Zhang, Y.; Zhang, Z.; Zhang, G.; Ye, Y.; Sun, K. Adv. Synth. Catal. 2021, 363, 3290. doi: 10.1002/adsc.v363.13 pmid: 30483684
[8]	(a) Chen, D.-J.; Chen, Z.-C. J. Chem. Res. 2000, 370.
	(b) Xu, Q.; Liang, C.-G.; Huang, X. Synth. Commun. 2003, 33, 2777. doi: 10.1081/SCC-120022165
[9]	(a) Guo, S.; Li, S.; Zhang, Z.; Yan, W.; Cai, H. Tetrahedron Lett. 2020, 61, 151566. doi: 10.1016/j.tetlet.2019.151566
	(b) Amri, N.; Wirth, T. Synlett 2020, 31, 1894. doi: 10.1055/s-0040-1707141
[10]	Clive, D. L. J.; Menchen, S. M. J. Org. Chem. 1980, 45, 2347. doi: 10.1021/jo01300a016
[11]	(a) Wang, P.-F.; Yi, W.; Ling, Y.; Ming, L.; Liu, G.-Q.; Zhao, Y. Chin. Chem. Lett. 2021, 32, 2587. doi: 10.1016/j.cclet.2021.02.050
	(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. doi: 10.1039/D1GC00049G
	(c) Liang, Z.-P.; Yi, W.; Wang, P.-F.; Liu, G.-Q.; Ling, Y. J. Org. Chem. 2021, 86, 5292. doi: 10.1021/acs.joc.1c00257
[12]	(a) Barnes, I.; Hjorth, J.; Mihalopoulos, N. Chem. Rev. 2006, 106, 940. pmid: 16522014
	(b) Wu, X.-F.; Natte, K. Adv. Synth. Catal. 2016, 358, 336. doi: 10.1002/adsc.201501007 pmid: 16522014
[13]	(a) Shi, M.; Wang, B.-Y.; Li, J. Eur. J. Org. Chem. 2005, 759.
	(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.
	(c) Tiecco, M.; Testaferri, L.; Tingoli, M.; Chianelli, D.; Bartoli, D. Tetrahedron Lett. 1989, 30, 1417. doi: 10.1016/S0040-4039(00)99480-2
	(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. doi: 10.1039/C7GC02803B
[15]	(a) Gancarz, R. A.; Kice, J. L. Tetrahedron Lett. 1981, 22, 1661. doi: 10.1016/S0040-4039(01)90404-6
	(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. doi: 10.1016/S0040-4039(00)87604-2
	(b) Kice, J. L.; McAfee, F.; Slebocka-Tilk, H. Tetrahedron Lett. 1982, 23, 3323. doi: 10.1016/S0040-4039(00)87605-4
	(c) Kang, S. I.; Kice, J. L. J. Org. Chem. 1985, 50, 2968. doi: 10.1021/jo00216a032
[17]	Singh, D.; Deobald, A. M.; Camargo, L. R. S.; Tabarelli, G.; Rodrigues, O. E. D.; Braga, A. L. Org. Lett. 2010, 12, 3288. doi: 10.1021/ol100558b
[18]	Loginova, E. I.; Nuretdinov, I. A.; Petrov, Y. A. Teor. Eksp. Khim. 1974, 10, 75.

叔丁基过氧化氢介导的磷酸硒酯合成

tert-Butyl Hydroperoxide-Mediated Synthesis of Phosphoroselenoates

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 7

References 18

Related Articles 15

Recommended Articles

Metrics

Comments

Entry	Oxidant	Solvent	Time/h	Isolated yield/%
1	PhIO	EtOAc	5	43
2	PhI(OAc)₂	EtOAc	5	35
3	K₂S₂O₈	EtOAc	5	45
4	(NH₄)₂S₂O₈	EtOAc	5	40
5	I₂O₅	EtOAc	5	26
6	Oxone	EtOAc	5	51
7	mCPBA	EtOAc	5	45
8	TBHP	EtOAc	5	65
9	O₂	EtOAc	5	30
10	TBHP	DMSO	5	88
11	TBHP	DMF	5	65
12	TBHP	EtOH	5	55
13	TBHP	THF	5	50
14	TBHP	Hexane	5	56
15	TBHP	Acetone	5	70
16^b	TBHP	DMSO	5	76
17^c	TBHP	DMSO	5	65
18	TBHP	DMSO	2	89
19	TBHP	DMSO	1	73
20	—	DMSO	2	trace

[1]	Liming Wang, Ke Li, Wanxuan Zhang. Organoselenium-Catalyzed Conversion of Oximes to Nitriles or Ketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1235-1240.
[2]	Yongxin Chen, Xin Guo, Yafeng Liu, Xueying Yang, Baohua Chen. Synthesis of 1,2,4-Triazolo[4,3-a]pyridines by I₂-Catalyzed Oxidative Coupling of 2-Aminopyridines with N-Tosylhydrazones [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3863-3869.
[3]	Ningbo Li, Li Xu, Rong Ma, Qi Fan, Bo Li, Jie Qiao, Rui Guo, Xinhua Xu. Synthesis and Antitumor Activities of Novel Organic Sulfur (Selenium) Tegafur Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2723-2734.
[4]	Fang Zhao, Wenjing Ye, Kai Wang. Advancement of Chiral Monodentate Phosphite Ligands in Asymmetric Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2650-2665.
[5]	Wenyi Li, Yinheng Tang, Wentao Ouyang, Yuhan Lu, Jinyang Chen, Weimin He. Electrochemical Selenylation of N-Unprotected Anilines for Consturcing 4-(Organylselanyl)anilines [J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4766-4772.
[6]	Yuanting Huang, Qian Chen. Recent Advances in C(sp³)—H Phosphorylation Based on Secondary Phosphine Oxides and Phosphite Esters [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4138-4153.
[7]	Jianqi Liu, Weiwei Fan, Hangxing Xiong, Jingyun Jiang, Hongju Zhan. Benzylic Oxidation Catalyzed by Cobalt(II)-Terpyridine Coordination Polymers [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4409-4414.
[8]	Shuhua He, Hang Zhang, Hongyu Wu, Shiyu Zhou, Yao Xiao, Xianhui You, Jinyang Chen. ICl-Catalyzed C_sp2—H Selenation of Aminocoumarin Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4378-4383.
[9]	Ge Yanyu, Kong Jing, Yang Chenggen, Yang Qian, Zhang Xu. Design and Synthesis of 1,2-Bis(4-(benzyloxy)phenyl)diselane: A Scavenger for Residual Copper [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1760-1765.
[10]	Wang Lingxiao, Li Ningbo, Wang Haojiang, Liu Wen, Diao Haipeng, Xu Xinhua. Efficient Synthesis of Unsymmetrical Selenides Promoted by Titanocene Perfluorobutanesulfonate/Zinc Catalytic System [J]. Chin. J. Org. Chem., 2019, 39(6): 1802-1807.
[11]	Feng Zhigang, Xie Xiaomin, Zhang Zhaoguo. Palladium-Catalyzed Cross-Coupling Reaction of Arenesulphonate with Phosphite [J]. Chin. J. Org. Chem., 2018, 38(4): 896-901.
[12]	Wang Yufeng, Yang Yajie, Huang Ling, Jie Kun, Guo Shengmei, Cai Hua. Iodine Catalyzed Kabachnik-Fields Reaction of Trialkyl Phosphites: Facile Access to Benzoxazine Containing Phosphorus [J]. Chin. J. Org. Chem., 2017, 37(12): 3220-3228.
[13]	Xing Aiping, Tian Mi, Wang Lailai. Novel Chiral C3-Symmetric Monophosphite Ligands: Synthsis and Catalytic Performance in Asymmetric Hydroformylation and 1,4-Conjugate Addition [J]. Chin. J. Org. Chem., 2016, 36(12): 2912-2919.
[14]	Ouyang Yuejun, Guo Cuixia, Qiu Renhua, Li Ningbo Chen Jinyang, Xu Xinxua. Iron-Mediated Cleavage of Se—Se Bond for the Synthesis of α-Arylseleno Carbonyl Compounds [J]. Chin. J. Org. Chem., 2015, 35(3): 731-734.
[15]	Xu Qing, Jia Xiaojuan, Li Xiaohui, Sun Qing, Zhou Yongbo, Yin Shuangfeng, Han Libiao. Copper-Catalyzed Aerobic Oxidative C-P Coupling of Arylboronic Acids and Diethyl Phosphite under Air [J]. Chin. J. Org. Chem., 2014, 34(7): 1340-1346.