Visible-Light-Promoted Multi-Component Reaction of α-Diazoesters to Construct Alkyl Phosphorodithioates

doi:10.6023/cjoc202410012

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (10): 3912-3922.DOI: 10.6023/cjoc202410012 Previous Articles Next Articles

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可见光促进α-重氮酯参与多组分反应合成烷基二硫代磷酸酯

冯亚萍^a^,^†, 黄健^b^,^†, 王英杰^b, 孙键^b, 南光明^a^,^*(), 魏伟^b^,^*()

^a 伊犁师范大学化学化工学院新疆维吾尔自治区教育厅天然产物化学与应用重点实验室新疆伊宁 835000
^b 曲阜师范大学化学与化工学院山东曲阜 273165

收稿日期:2024-10-22 修回日期:2024-12-09 发布日期:2025-01-10
作者简介:
^† 共同第一作者.
基金资助:
新疆维吾尔自治区教育厅普通高等学校天然产物化学与应用重点实验室(2024YSHXZD01)

Visible-Light-Promoted Multi-Component Reaction of α-Diazoesters to Construct Alkyl Phosphorodithioates

Yaping Feng^a, Jian Huang^b, Yingjie Wang^b, Jian Sun^b, Guangming Nan^a^,^*(), Wei Wei^b^,^*()

^a Key Lab of Natural Product Chemistry and Application at Universities of Education Department of Xinjiang Uygur Autonomous Region, School of Chemistry and Chemical Engineering, Yili Normal University, Yining, Xinjiang 835000
^b School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165

Received:2024-10-22 Revised:2024-12-09 Published:2025-01-10
Contact: * nanguangming02@sohu.com; weiweiqfnu@163.com
About author:
^† These authors contributed equally to this wor).
Supported by:
Foundation of Key Lab of Natural Product Chemistry and Application at Universities of Education Department of Xinjiang Uygur Autonomous Region(2024YSHXZD01)

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Abstract

Visible-light-promoted multi-component reaction of α-diazoesters, tetrahydrofuran, P₄S₁₀ and alcohols to construct alkyl phosphorodithioates has been developed. The present method, which utilizes 10 W blue LED lamps as clean energy source and Cs₂CO₃ as a base, offers an efficient approach to access a series of alkyl phosphorodithioates at room temperature. The reaction has the advantages of mild condition, clean energy source, and non metal-pollution.

Key words: visible-light, α-diazoester, multi-component reaction, P₄S₁₀, alkyl phosphorodithioate

Cite this article

Yaping Feng, Jian Huang, Yingjie Wang, Jian Sun, Guangming Nan, Wei Wei. Visible-Light-Promoted Multi-Component Reaction of α-Diazoesters to Construct Alkyl Phosphorodithioates[J]. Chinese Journal of Organic Chemistry, 2025, 45(10): 3912-3922.

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Fig. & Tab. 6

References 17

[1]	(a) Roux, L.; Priet, S.; Payrot, N.; Weck, C.; Fournier, M.; Zoulim, F.; Balzarini, J.; Canard, B.; Alvarez, K. Eur. J. Med. Chem. 2013, 63, 869.
	(b) Myers, D. K.; Mendel, B.; Gersmann, H. R.; Ketelaar, J. A. A. Nature 1952, 170, 805.
	(c) Gaynor, J. W.; Brazier, J.; Cosstick, R. Nucleosides, Nucleotides Nucleic Acids 2007, 26, 709.
	(d) Melnikov, N. N.; Busbey, R. L.; Gunther, F. A.; Gunther, J. D. Chemistry of Pesticides, Springer New York, 2012.
	(e) Kazemi, M.; Tahmasbi, A.; Valizadeh, R.; Naserian, A.; Soni, A. Agric. Sci. Res. J. 2012, 2, 512.
	(f) Kumar, T. S.; Yang, T.; Mishra, S.; Cronin, C.; Chakraborty, S.; Shen, J.-B.; Liang, B.-T.; Jacobson, K. A. J. Med. Chem. 2013, 56, 902.
[2]	Mosey, N. J.; Woo, T. K. J. Phys. Chem. A 2003, 107, 5058.
[3]	(a) Gurevich, P. A.; Komina, T. V.; Klimentova, G. Y.; Zykova, T. V.; Ruzal, G. I. Khim.-Farm. Zh. 1984, 18, 489. pmid: 19481235
	(b) Smirnova, T. V.; Kozenasheva, L. Y.; Kurkovskaya, L. N. Zh. Obshch. Khim. 1983, 53, 1734. pmid: 19481235
	(c) Miller, B. J. Am. Chem. Soc. 1960, 82, 6205. pmid: 19481235
	(d) Miller, B. Tetrahedron 1964, 20, 2069. pmid: 19481235
	(e) Kaboudin, B.; Emadi, S.; Hadizadeh, A. Bioorg. Chem. 2009, 37, 101. doi: 10.1016/j.bioorg.2009.05.002 pmid: 19481235
[4]	(a) Kozlov, V. A.; Churusova, S. G.; Yarovenko, S. V.; Kononova, O. A.; Negrebetskii, V. V.; Grapov, A. F. Zh. Obshch. Khim. 1994, 64, 1439.
[5]	(a) Dybowski, P.; Skowronska, A. Synthesis 1990, 7, 609.
	(b) Skowronska, A.; Dybowski, P. Heteroat. Chem. 1991, 2, 55.
[6]	Li, Z.; Zhou, Z.; Li, K.; Wang, L.; Zhou, Q.; Tang, C. Tetrahedron Lett. 2002, 43, 7609.
[7]	(a) Yu, J.; Shi, F.; Gong, L-Z. Acc. Chem. Res. 2011, 44, 1156.
	(b) Levi, L.; Müller, T. J. J. Chem. Soc. Rev. 2016, 45, 2825.
[8]	Ozturk, T.; Ertas, E.; Mert, O. Chem. Rev. 2010, 110, 3419. doi: 10.1021/cr900243d pmid: 20429553
[9]	(a) Mastin, T. W.; Norman, G. R.; Weilmuenster, E. A. J. Am. Chem. Soc. 1945, 67, 1662.
	(b) Fletcher, J. H.; Hamilton, J. C.; Hechenbleikner, I.; Hoegberg, E. I.; Sertl, B. J.; Cassaday, J. T. J. Am. Chem. Soc. 1950, 72, 2461.
[10]	Wang, J.; Han, F.; Hao, S.; Tang, Y.-J.; Xiong, C.; Xiong, L.; Li, X.; Lu, J.; Zhou, Q. J. Org. Chem. 2022, 87, 12844.
[11]	(a) Qu, C.; Lv, Y.; Huang, J.; Ma, C.; Yue, H.; Wei, W.; Yi, D. Green Chem. 2023, 25, 10678.
	(b) Qu, C.; Wang, Y.; Lv, Y.; Yue, H.; Wei, W.; Yi, D. Org. Chem. Front. 2024, 11, 171.
	(c) Chen, X.-M.; Song, L.; Pan, J.; Zeng, F.; Xie, Y.; Wei, W.; Yi, D. Chin. Chem. Lett. 2024, 35, 110112.
	(d) Chen, X.-M.; Huang, J.; Pan, J.; Xie, Y.; Zeng, F.; Wei, W.; Yi, D. Org. Lett. 2024, 26, 3883.
	(e) Hao, J.; Lv, Y.; Tian, S.; Ma, C.; Cui, W.; Yue, H.; Wei, W.; Yi, D. Chin. Chem. Lett. 2024, 35, 109513.
[12]	(a) Liu, L.; Zhang, J. Chem. Soc. Rev. 2016, 45, 506. doi: 10.1039/c5cs00821b pmid: 26658761
	(b) Li, Q.; Li, M.; Shi, S.; Ji, X.; He, C.; Jiang, B.; Hao, J. Chin. J. Org. Chem. 2020, 40, 384 (in Chinese). pmid: 26658761
	(李庆雪, 李梦伟, 时绍青, 季晓霜, 何春兰, 姜波, 郝文娟, 有机化学, 2020, 40, 384.) doi: 10.6023/cjoc201909041 pmid: 26658761
	(c) Cai, B.; Xuan, J. Chin. J. Org. Chem. 2021, 41, 4565 (in Chinese). pmid: 26658761
	(蔡宝贵, 宣俊, 有机化学, 2021, 41, 4565.) doi: 10.6023/cjoc202109040 pmid: 26658761
	(d) Zhao, B.; Yang, L.; Cheng, K.; Zhou, L.; Wan, J-P. Chin. J. Org. Chem. 2021, 41, 4723 (in Chinese). pmid: 26658761
	(赵保丽, 杨良凤, 程凯, 周丽云, 万结平, 有机化学, 2021, 41, 4723.) pmid: 26658761
[13]	(a) Yang, Z.; Stivanin, M. L.; Jurberg, I. D.; Koenigs, R. M. Chem. Soc. Rev. 2020, 49, 6833.
	(b) Lv, Y.; Ding, H.; You, J.; Wei, W.; Yi, D. Chin. Chem. Lett. 2024, 35, 109107.
	(c) Wang, Z.; Meng, N.; Lv, Y.; Wei, W.; Yue, H.; Zhong, G. Chin. Chem. Lett. 2023, 34, 107599.
	(d) Qu, C.; Liu, R.; Wang, Z.; Lv, Y.; Yue, H.; Wei, W. Green Chem. 2022, 24, 4915.
	(e) Cai, B.-G.; Li, Q.; Empel, C.; Li, L.; Koenigs, R. M.; Xuan, J. ACS Catal. 2022, 12, 11129.
[14]	(a) Liu, R.; Fu, S.; Chu, X.; Zhang, L.; Ding, R.; Zhao, X.; Yue, H.; Wei, W. Chin. J. Org. Chem. 2022, 42, 2462 (in Chinese).
	(刘瑞生, 付双敏, 楚秀民, 张灵莉, 丁柔, 赵先恩, 岳会兰, 魏伟, 有机化学, 2022, 42, 2462.) doi: 10.6023/cjoc202204014
	(b) Wang, Z.; Liu, Q.; Liu, R.; Ji, Z.; Li, Y.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2022, 33, 1479.
	(c) Meng, N.; Lv, Y.; Liu, Q.; Liu, R.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2021, 32, 2458.
	(d) Zhang, M.; Nan, G.; Zhao, X.; Wei, W. Chin. J. Org. Chem. 2022, 42, 4315 (in Chinese).
	(张孟琪, 南光明, 赵晓辉, 魏伟, 有机化学, 2022, 42, 4315.) doi: 10.6023/cjoc202209013
[15]	Stivanin, M. L.; Gallo, R. D. C.; Spadeto, J. P. M.; Cormanich, R. A.; Jurberg, I. D. Org. Chem. Front. 2022, 9, 1321.
[16]	(a) He, F.; Pei, C.; Koenigs, R. M. Chem. Commun. 2020, 56, 599.
	(b) Cheng, R.; Qi, C.; Wang, L.; Xiong, W.; Liu, H.; Jiang, H. Green Chem. 2020, 22, 4890.
	(c) Li, Q.; Cai, B.-G.; Li, L.; Xuan, J. Org. Lett., 2021, 23, 6951.
	(d) Liu, R.; Liu, Q.; Meng, H.; Ding, H.; Hao, J.; Ji, Z.; Yue, H.; Wei, W. Org. Chem. Front. 2021, 8, 1970.
[17]	Yang, J.; Duan, J.; Wang, G.; Zhou, H.; Ma, B.; Wu, C.; Xiao, J. Org. Lett. 2020, 22, 7284.

Entry	Base	Light source/nm	Solvent (V∶V)	Yield^b/% of 5a	Yield^b/% of 6a
1	Et₃N	390~465	EtOH/THF (1∶3)	50	31
2	Et₃N	440~465	EtOH/THF (1∶3)	42	28
3	Et₃N	450~465	EtOH/THF (1∶3)	37	31
4	Et₃N	460~465	EtOH/THF (1∶3)	57	30
5	Et₃N	470~485	EtOH/THF (1∶3)	48	35
6	Et₃N	520~525	EtOH/THF (1∶3)	Trace	58
7	Et₃N	460~465	EtOH/THF (1∶4)	51	29
8	Et₃N	460~465	EtOH/THF (1∶5)	48	32
9	Et₃N	460~465	EtOH/THF (1∶6)	46	27
10	Et₃N	460~465	EtOH/THF (1∶9)	29	26
11	Et₃N	460~465	EtOH/THF (1∶2)	47	23
12	Et₃N	460~465	EtOH/THF (2∶1)	25	25
13	Cs₂CO₃	460~465	EtOH/THF (1∶3)	63	32
14	K₂CO₃	460~465	EtOH/THF (1∶3)	42	36
15	DBU	460~465	EtOH/THF (1∶3)	45	41
16	KOH	460~465	EtOH/THF (1∶3)	36	27
17	^tBuOK	460~465	EtOH/THF (1∶3)	29	28
18^c	Cs₂CO₃	460~465	EtOH/THF (1∶3)	42	18
19^d	Cs₂CO₃	460~465	EtOH/THF (1∶3)	47	17
20^e	Cs₂CO₃	460~465	EtOH/THF (1∶3)	52	16
21^f	Cs₂CO₃	460~465	EtOH/THF (1∶3)	43	24
21^g	Cs₂CO₃	460~465	EtOH/THF (1∶3)	0	42

Entry	Base	Light source/nm	Solvent (V∶V)	Yield^b/% of 5a	Yield^b/% of 6a
1	Et₃N	390~465	EtOH/THF (1∶3)	50	31
2	Et₃N	440~465	EtOH/THF (1∶3)	42	28
3	Et₃N	450~465	EtOH/THF (1∶3)	37	31
4	Et₃N	460~465	EtOH/THF (1∶3)	57	30
5	Et₃N	470~485	EtOH/THF (1∶3)	48	35
6	Et₃N	520~525	EtOH/THF (1∶3)	Trace	58
7	Et₃N	460~465	EtOH/THF (1∶4)	51	29
8	Et₃N	460~465	EtOH/THF (1∶5)	48	32
9	Et₃N	460~465	EtOH/THF (1∶6)	46	27
10	Et₃N	460~465	EtOH/THF (1∶9)	29	26
11	Et₃N	460~465	EtOH/THF (1∶2)	47	23
12	Et₃N	460~465	EtOH/THF (2∶1)	25	25
13	Cs₂CO₃	460~465	EtOH/THF (1∶3)	63	32
14	K₂CO₃	460~465	EtOH/THF (1∶3)	42	36
15	DBU	460~465	EtOH/THF (1∶3)	45	41
16	KOH	460~465	EtOH/THF (1∶3)	36	27
17	^tBuOK	460~465	EtOH/THF (1∶3)	29	28
18^c	Cs₂CO₃	460~465	EtOH/THF (1∶3)	42	18
19^d	Cs₂CO₃	460~465	EtOH/THF (1∶3)	47	17
20^e	Cs₂CO₃	460~465	EtOH/THF (1∶3)	52	16
21^f	Cs₂CO₃	460~465	EtOH/THF (1∶3)	43	24
21^g	Cs₂CO₃	460~465	EtOH/THF (1∶3)	0	42

可见光促进α-重氮酯参与多组分反应合成烷基二硫代磷酸酯

Visible-Light-Promoted Multi-Component Reaction of α-Diazoesters to Construct Alkyl Phosphorodithioates

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