Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst

doi:10.6023/cjoc202306023

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (2): 584-592.DOI: 10.6023/cjoc202306023 Previous Articles Next Articles

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无光催化剂条件下可见光诱导炔基碘和亚磺酸钠偶联反应

陈雯雯^*(), 张琴, 张松月, 黄芳芳, 张馨尹, 贾建峰^*()

山西师范大学化学与材料科学学院磁性分子与磁信息材料教育部重点实验室山西太原 030031

收稿日期:2023-06-26 修回日期:2023-09-20 发布日期:2023-10-23
作者简介:
^† 作者对文章贡献一致
基金资助:
山西省自然科学基金(202203021221134); 山西省研究生教育教学改革课题(2022YJJG136)

Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst

Wenwen Chen(), Qin Zhang, Songyue Zhang, Fangfang Huang, Xinyin Zhang, Jianfeng Jia()

Key Laboratory of Magnetic Molecules & Magnetic Information Materials Ministry of Education, School of Chemical and Material Science, Shanxi Normal University, Taiyuan 030031

Received:2023-06-26 Revised:2023-09-20 Published:2023-10-23
Contact: * E-mail: chenww@sxnu.edu.cn; jiajf@dns.sxnu.edu.cn
About author:
^† The authors contributed equally to this work.
Supported by:
Natural Science Foundation of Shanxi Province(202203021221134); Postgraduate Education Teaching Reform Topic of Shanxi Province(2022YJJG136)

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Abstract

The cross-coupling reaction between alkynyl iodide and sodium sulphinate catalyzed by visible light, leading to the construction of acetylene sulfone, is reported. The synthesis method is simple and green, and does not require any photo- catalyst and additive. The reaction has high efficiency and good functional group compatibility. In addition, the scale-up experiment can also obtain good yield, which further proves the practical application value of the reaction.

Key words: alkyne sulfone, visible light, alkynyl iodine, sodium sulphinate, coupling reaction

Cite this article

Wenwen Chen, Qin Zhang, Songyue Zhang, Fangfang Huang, Xinyin Zhang, Jianfeng Jia. Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 584-592.

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Fig. & Tab. 10

References 16

[1]	Feng, M. H.; Tang, B. Q.; Liang, S. H.; Jiang, X. F. Curr. Top. Med. Chem. 2016, 16, 1200. doi: 10.2174/1568026615666150915111741
[2]	Balaburski, G. M.; Leu, J. I.-J.; Beeharry, N.; Hayik, S.; Andrake, M. D.; Zhang, G.; Herlyn, M.; Villanueva, J.; Dunbrack Jr, R. L.; Yen, T.; George, D. L.; Murphy, M. E. Mol. Cancer Res. 2013, 11, 219. doi: 10.1158/1541-7786.MCR-12-0547-T pmid: 23303345
[3]	Selling, H. A.; Tempe, A. Pestic. Sci. 1976, 7, 19. doi: 10.1002/ps.v7:1
[4]	(a) Huang, X.; Duan, D.; Zheng, W. ChemInfor. 2003, 34, 1958.
	(b) Xie, M.; Wang, J.; Gu, X.; Sun, Y.; Wang, S. Org. Lett. 2006, 8, 431. doi: 10.1021/ol052640i
[5]	(a) Xiao, Q.; Lu, M.; Deng, Y.; Jian, J.-X.; Tong, Q.-X.; Zhong, J.-J. Org. Lett. 2021, 23, 9303. doi: 10.1021/acs.orglett.1c03700
	(b) Jia, J.; Ho, Y. A.; Bulow, R. F. Chemistr. 2018, 24, 14054.
	(c) Song, W.; Zheng, N.; Li, M.; Dong, K.; Li, J.; Ullah, K.; Zheng, Y. Org. Lett. 2018, 20, 6705. doi: 10.1021/acs.orglett.8b02794
	(d) Wang, S.; Liu, C.; Jia, J.; Zha, C.; Xie, M.; Zhang, N. Tetrahedro. 2016, 72, 6684. doi: 10.1016/j.tet.2016.08.081
	(e) Zhou, X.; Yu, S.; Qi, Z.; Li, X. Sci. China Chem. 2015, 58, 1297. doi: 10.1007/s11426-015-5408-8
[6]	(a) Fang, K.; Xie, M.; Zhang, Z.; Ning, P.; Shu, G. Tetrahedron Lett. 2013, 54, 3819. doi: 10.1016/j.tetlet.2013.05.049 pmid: 30924668
	(b) Guo, A.; Han, J. B.; Zhu, L.; Wei, Y. ; Org. Lett. 2019, 21, 2927. doi: 10.1021/acs.orglett.9b00985 pmid: 30924668
	(c) Jin, W.; Wu, M.; Xiong, Z.; Zhu, G. Chem. Commun. 2018, 54, 7924. doi: 10.1039/C8CC03105C pmid: 30924668
[7]	(a) Truce, W. E.; Hill, H. E.; Boudakia, M. M. J. Am. Chem. Soc. 1956, 78, 2760. doi: 10.1021/ja01593a030
	(b) Laba, V. I.; Polievktov, M. K.; Prilezhaeva, E. N.; Mairanovskii, S. G. Bull. Acad. Sci. USSR. Div. Chem. Sci. 1969, 18, 2004. doi: 10.1007/BF00906610
	(c) Corlay, H.; Lewis, R. T.; Motherwell, W. B.; Shipman, M. Tetrahedro. 1995, 51, 3303. doi: 10.1016/0040-4020(95)00052-A
	(d) Zaburdaeva, E. A.; Dodonov, V. A. Russ. Chem. Bull. 2011, 185.
[8]	(a) Truce, W. E.; Wolf, G. C. J. Org. Chem. 1971, 36, 1727. doi: 10.1021/jo00812a001
	(b) Lee, J. W.; Kim, T. H.; Oh, D. Y. Synth. Commun. 1989, 19, 2633. doi: 10.1080/00397918908053056
	(c) Nair, V.; Augustine, A.; Suja, T. D. Synthesi. 2002, 2259.
	(d) Qi, D.; Dong, W.; Peng, Z.; Zhang, Y.; An, D. Tetrahedro. 2019, 75, 130427. doi: 10.1016/j.tet.2019.06.035
[9]	(a) Miura, T.; Kobayashi, M. J. Chem. Soc.. Chem. Commun. 1982, 438.
	(b) Bhaskar, R. D.; Chandrasekhar, B. N.; Padmavathi, V.; Padmaja, A. Tetrahedro. 1997, 53, 17351. doi: 10.1016/S0040-4020(97)10159-4
	(c) Qian, H.; Huang, X. Tetrahedron Lett. 2002, 43, 1059. doi: 10.1016/S0040-4039(01)02330-9
[10]	Suzuki, H.; Abe, H. Tetrahedron Lett. 1996, 37, 3717. doi: 10.1016/0040-4039(96)00649-1
[11]	(a) Liu, Z. D.; Chen, Z. C. Synth. Commun. 1992, 22, 1997. doi: 10.1080/00397919208021333 pmid: 33978047
	(b) Huang, X.; Zhu, Q. Tetrahedron Lett. 2001, 42, 6373. doi: 10.1016/S0040-4039(01)01274-6 pmid: 33978047
	(c) Wei, W.; Wen, J.; Yang, D.; Jing, H.; You, J.; Wang, H. RSC Adv. 2015, 5, 4416. doi: 10.1039/C4RA13998D pmid: 33978047
	(d) Raghuvanshi, D. S.; Verma, N. Org. Biomol. Chem. 2021, 19, 4760. doi: 10.1039/d1ob00036e pmid: 33978047
	(e) Meesin, J.; Katrun, P.; Pareseecharoen, C.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Kuhakarn, C. J. Org. Chem. 2016, 81, 2744. doi: 10.1021/acs.joc.5b02810 pmid: 33978047
	(f) Dai, C.; Wang, J.; Deng, S.; Zhou, C.; Zhang, W.; Zhu, Q.; Tang, X. RSC Adv. 2017, 7, 36112. doi: 10.1039/C7RA07105A pmid: 33978047
	(g) Wang, L.; Wei, W.; Yang, D.; Cui, H.; Yue, H.; Wang, H. Tetrahedron Lett. 2017, 58, 4799. doi: 10.1016/j.tetlet.2017.11.029 pmid: 33978047
	(h) Mo, Z. Y.; Zhang, Y. Z.; Huang, G. B.; Wang, X. Y.; Pan, Y. M.; Tang, H. T. Adv. Synth. Catal. 2020, 362, 2160. doi: 10.1002/adsc.v362.11 pmid: 33978047
	(i) Meng, X.; Xu, H.; Cao, X.; Cai, X. M.; Luo, J.; Wang, F.; Huang, S. Org. Lett. 2020, 22, 6827. doi: 10.1021/acs.orglett.0c02341 pmid: 33978047
	(j) Gong, X.; Yang, M.; Liu, J. B.; He, F. S.; Wu, J. Org. Chem. Fron. 2020, 7, 938. pmid: 33978047
[12]	(a) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Acc. Chem. Res. 2016, 49, 1911. doi: 10.1021/acs.accounts.6b00254
	(b) Zhou, Q. Q.; Zou, Y. Q.; Lu, L. Q.; Xiao, W. J. Angew. Chem.. Int. Ed. 2019, 58, 1586. doi: 10.1002/anie.v58.6
[13]	Wang, X.; Li, X.; Tian, B.; Xiao, H.; Chen, W.; Wu, H.; Jia, J. Arabian J. Chem. 2022, 15, 103708. doi: 10.1016/j.arabjc.2022.103708
[14]	(a) Zhang, L.; Wei, C.; Wu, J.; Liu, D.; Yao, Y.; Chen Z.; Liu, J, ; Yao, C.-J.; Li, D.; Yang, R.; Xia, Z. Chem. Sci. 2022, 13, 7475. doi: 10.1039/D2SC01933G
	(b) Amos, S. G. E.; Cavalli, D.; Vaillant, F. L.; Waser, J. Angew. Chem.. Int. Ed. 2021, 60, 23827. doi: 10.1002/anie.v60.44
[15]	(a) Fang, Z; Zhang, Y.; Zhang, Z.; Song, Q.; Wu, Y.; Liu, Z.; Ning, Y. Org. Lett. 2022, 6374.
	(b) Aleti, R. R.; Festa, A. A.; Storozhenko, O. A.; Bondarev, V. L.; Segida, O. O.; Paveliev, S. A.; Rybakov, V. B.; Varlamov, A. V.; Voskressensky, L. G. Org. Lett. 2022, 24, 9337. doi: 10.1021/acs.orglett.2c03985
	(c) Wang, Y.; Tang, K.; Liu, Z.; Ning, Y. Chem. Commun. 2020, 56, 13141. doi: 10.1039/D0CC05849A
[16]	Chen, P.; Zhu, C.; Zhu, R.; Wu, W.; Jiang, H. Chem. Asian J. 2017, 12, 1875. doi: 10.1002/asia.v12.15

Entry	Light source	Atmosphere	I₂	Cat.	Yield^b/%
1^c^,^d	White LED	O₂	I₂	BiOCl	54
2^c	White LED	O₂	I₂	—	42
3^d	White LED	O₂	—	BiOCl	62
4	White LED	O₂	—	—	60
5	Blue LED	O₂	—	—	39
6	Red LED	O₂	—	—	29
7	Green LED	O₂	—	—	35
8	White LED	Air	—	—	60
9	White LED	N₂	—	—	44
10^e	—	Air	—	—	27
11^f	—	Air	—	—	16

Entry	Light source	Atmosphere	I₂	Cat.	Yield^b/%
1^c^,^d	White LED	O₂	I₂	BiOCl	54
2^c	White LED	O₂	I₂	—	42
3^d	White LED	O₂	—	BiOCl	62
4	White LED	O₂	—	—	60
5	Blue LED	O₂	—	—	39
6	Red LED	O₂	—	—	29
7	Green LED	O₂	—	—	35
8	White LED	Air	—	—	60
9	White LED	N₂	—	—	44
10^e	—	Air	—	—	27
11^f	—	Air	—	—	16

Entry	Solvent	Additive	Yield^b/%
1	1,4-Dioxane	—	68
2	CH₃CN	—	76
3	MeOH	—	26
4	DCE	—	67
5	DMF	—	31
6	Toluene	—	43
7	DMSO	—	19
8	H₂O	—	38
9	TFE	—	61
10	C₇H₅F₃	—	45
11^c	CH₃CN/H₂O	—	57
12^d	CH₃CN/H₂O	—	62
13	CH₃CN	K₂CO₃(1.0 equiv.)	58
14	CH₃CN	NEt₃(1.0 equiv.)	33
15	CH₃CN	HCl (1.0 equiv.)	63
16	CH₃CN	CH₃COOH (1.0 equiv.)	54
17	CH₃CN	TBAI (0.2 equiv.)	33

Entry	Solvent	Additive	Yield^b/%
1	1,4-Dioxane	—	68
2	CH₃CN	—	76
3	MeOH	—	26
4	DCE	—	67
5	DMF	—	31
6	Toluene	—	43
7	DMSO	—	19
8	H₂O	—	38
9	TFE	—	61
10	C₇H₅F₃	—	45
11^c	CH₃CN/H₂O	—	57
12^d	CH₃CN/H₂O	—	62
13	CH₃CN	K₂CO₃(1.0 equiv.)	58
14	CH₃CN	NEt₃(1.0 equiv.)	33
15	CH₃CN	HCl (1.0 equiv.)	63
16	CH₃CN	CH₃COOH (1.0 equiv.)	54
17	CH₃CN	TBAI (0.2 equiv.)	33

无光催化剂条件下可见光诱导炔基碘和亚磺酸钠偶联反应

Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst

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Entry	n(2a)∶n(1a)	V(solvent)/mL	Time/h	Yield^b/%
1	3.0∶1.0	2	21	36
2	2.5∶1.0	2	21	52
3	1.5∶1.0	2	21	50
4	2.0∶1.0	2	21	76
5	1.0∶1.0	2	21	22
6	1.0∶1.5	2	21	31
7	1.0∶2.0	2	21	35
8	2.0∶1.0	1	21	56
9	2.0∶1.0	3	21	64
10	2.0∶1.0	2	24	80
11	2.0∶1.0	2	27	65
12	2.0∶1.0	2	30	71
13	2.0∶1.0	2	33	63
14	2.0∶1.0	2	18	63
15	2.0∶1.0	2	15	62

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