Nickel-Catalyzed Coupling of 1,2-Diarylthio-1,2-diarylalkenes with Grignard Reagents for Synthesis of Multi-substituted Alkenes

doi:10.6023/cjoc201904050

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2946-2951.DOI: 10.6023/cjoc201904050 Previous Articles Next Articles

Special Issue: 碳氢活化合辑2018-2019

NOTES

镍催化(Z)-1,2-二芳硫基-1,2-二芳基烯烃与格氏试剂偶联反应制备多取代烯烃

吴燕, 罗凡, 潘世敏, 李玉涵, 何树华^*()

长江师范学院化学化工学院无机特种材料重庆市重点实验室涪陵 408000

收稿日期:2019-04-20 修回日期:2019-05-14 发布日期:2019-06-12
通讯作者: 何树华 E-mail:thshuhua@163.com
基金资助:
重庆市基础前沿研究(Cstc2018jcyjAX0721);长江师范学院青年人才成长计划(No. 2018QNRC11)

Nickel-Catalyzed Coupling of 1,2-Diarylthio-1,2-diarylalkenes with Grignard Reagents for Synthesis of Multi-substituted Alkenes

Wu, Yan, Luo, Fan, Pan, Shimin, Li, Yuhan, He, Shuhua^*()

Chongqing Key Laboratory of Inorganic Special Functional Materials, College of Chemistry and Chemical Engineering, Yangtze Normal University, Fuling 408000

Received:2019-04-20 Revised:2019-05-14 Published:2019-06-12
Contact: He, Shuhua E-mail:thshuhua@163.com
Supported by:
Project supported by the Basic and Frontier Research Project of Chongqing City(Cstc2018jcyjAX0721);the Youth Talent Growth Plan Project of Yangtze Normal University(No. 2018QNRC11)

A convenient protocol for the synthesis of multi-substituted alkenes from (Z)-1,2-diarylthio-1,2-diarylalkenes with Grignard reagents was developed via the highly selective coupling of (Z)-1,2-diarylthio-1,2-diarylalkenes catalyzed by 5.0 mol% NiCl₂(dppe). The leaving organosulfur group could be converted to diaryldisulfide after hydrolysis and oxidation, which realized the recycling of sulfur resources, meeting the requirements of green chemistry. This process tolerated to different (Z)-1,2-diarylthio-1,2-diarylalkenes and Grignard reagents to deliver products in good to excellent yields, providing an efficient route to multi-substituted alkenes.

Key words: nickel-catalyzed coupling, multi-substituted alkenes, (Z)-1,2-diarylthio-1,2-diarylalkenes, Grignard reagents

Cite this article

Wu, Yan, Luo, Fan, Pan, Shimin, Li, Yuhan, He, Shuhua. Nickel-Catalyzed Coupling of 1,2-Diarylthio-1,2-diarylalkenes with Grignard Reagents for Synthesis of Multi-substituted Alkenes[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2946-2951.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 3

References 40

[1]	(a) Witing, G.; Geissler, G. Justus Liebigs Ann. Chem. 1953,44.
	(b) Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 619.
[2]	Lu, L.-H.; Wang, Z.; Xia, W.; Cheng, P.; Zhang, B.; Cao, Z.; He, W.-M . Chin. Chem. Lett. 2019, 30, 1237. doi: 10.1016/j.cclet.2019.04.033
[3]	Caturla, F.; Amat, M.; Reinoso, R. F.; Córdoba, M.; Warrellow, G. Bioorg. Med. Chem. Lett. 2006, 16, 3209. doi: 10.1016/j.bmcl.2006.03.052
[4]	Zhang, Y.-H.; Shi, B.-F.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 5072. doi: 10.1021/ja900327e
[5]	Moragas, T.; Cornella, J.; Martin, R. J. Am. Chem. Soc. 2014, 136, 17702. doi: 10.1021/ja509077a
[6]	Oonishi, Y.; Ogura, J.; Sato, Y. Tetrahedron Lett. 2007, 48, 7505. doi: 10.1016/j.tetlet.2007.08.061
[7]	Coulter, M. M.; Dornan, P. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932. doi: 10.1021/ja901915u
[8]	Guo, R.; Huang, J.; Zhao, X. ACS Catal. 2018, 8, 926. doi: 10.1021/acscatal.7b03829
[9]	Zhou, C. X.; Larock, R. C. J. Org. Chem. 2005, 70, 3765. doi: 10.1021/jo048265+
[10]	Takahashi, A.; Kirio, Y.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1989, 111, 643. doi: 10.1021/ja00184a036
[11]	Oishi, S.; Miyamoto, K.; Niida, A.; Yamamoto, M.; Ajito, K.; Tamamura, H.; Otaka, A.; Kuroda, Y.; Asai, A.; Fujii, N. Tetrahedron 2006, 62, 1416. doi: 10.1016/j.tet.2005.11.033
[12]	Misumi, Y.; Masuda, T. Macromolecules 1998, 31, 7572. doi: 10.1021/ma981265p
[13]	Hall, H. K. J. Angew. Chem., Int. Ed. 1983, 22, 440. doi: 10.1002/(ISSN)1521-3773
[14]	Schreivogel, A.; Maurer, J.; Winter, R.; Baro, A.; Laschat, S. Eur. J. Org. Chem. 2010, 2006, 3395. doi: 10.1002/(ISSN)1099-0690
[15]	Urriolabeitia, E. P.; Villuendas, P.; Ruiz, S.; Vidossich, P.; Lledós, A . Chem-Eur. J. 2018, 24, 13124. doi: 10.1002/chem.201802546
[16]	Trost, B. M.; Tracy, J. S. ACS Catal. 2019, 9, 1584. doi: 10.1021/acscatal.8b04567
[17]	Wang, Q.; Liu, Z.; Lou, J.; Yu, Z. Org. Lett. 2018, 20, 6007. doi: 10.1021/acs.orglett.8b02253
[18]	He, Z.; Kirchberg, S.; Fröhlich, R.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 3699. doi: 10.1002/anie.v51.15
[19]	Wu, C.; Hong, L.; Shu, H.; Zhou, Q.-H.; Wang, Y.; Sun, M.; Jiang, S.; Cao, Z.; He, W.-M . ACS Sustainable Chem. Eng. 2019, 7, 8798. doi: 10.1021/acssuschemeng.9b00708
[20]	Itami, K.; Mineno, M.; Muraoka, N.; Yoshida, J. J. Am. Chem. Soc. 2004, 126, 11778. doi: 10.1021/ja045858t
[21]	Mckinley, N. F.; O’Shea, D. F. J. Org. Chem. 2006, 71, 9552. doi: 10.1021/jo061949s
[22]	Nishihara, Y.; Miyasaka, M.; Okamoto, M.; Takahashi, H.; Inoue, E.; Tanemura, K.; Takagi, K. J. Am. Chem. Soc. 2007, 129, 12634. doi: 10.1021/ja075234y
[23]	Suero, M. G.; Bayle, E. D.; Collins, B. S. L.; Gaunt, M. J. J. Am. Chem. Soc. 2013, 135, 5332. doi: 10.1021/ja401840j
[24]	Alfaro, R.; Parra, A.; Aleman, J.; Ruano, J. L. G.; Tortosa, M. J. Am. Chem. Soc. 2012, 134, 15165. doi: 10.1021/ja307670k
[25]	Itami, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2003, 125, 14670. doi: 10.1021/ja037566i
[26]	Yoshida, H.; Kageyuki, I.; Takaki, K. Org. Lett. 2013, 15, 952. doi: 10.1021/ol4001526
[27]	Reiser, O . Angew. Chem., Int. Ed. 2006, 45, 2838. doi: 10.1002/(ISSN)1521-3773
[28]	Iwasaki, M.; Topolovčan, N.; Hu, H.; Nishimura, Y.; Gagnot, G.; Na, N. R.; Nakajima, K.; Nishihara, Y. Org. Lett. 2016, 18, 1642. doi: 10.1021/acs.orglett.6b00503
[29]	Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J. Org. Lett. 2005, 7, 1219. doi: 10.1021/ol047504c
[30]	Jiang, H.; Tang, X.; Xu, Z.; Wang, H.; Han, K.; Yang, X.; Zhou, Y.; Feng, Y.-L.; Yu, X.-Y.; Gui, Q. Org. Biomol. Chem. 2019, 17, 2715. doi: 10.1039/C8OB02992J
[31]	Bouchet, L. M.; Penenory, A. B.; Robert, M.; Arguello, J. E. RSC Adv. 2015, 5, 11753. doi: 10.1039/C4RA16154H
[32]	Prasad, C. D.; Sattar, M.; Kumar, S. Org. Lett. 2017, 19, 774. doi: 10.1021/acs.orglett.6b03735
[33]	Chen, J.; Chen, S.; Xu, X.; Tang, Z.; Au, C. T.; Qiu, R. J. Org. Chem. 2016, 81, 3246. doi: 10.1021/acs.joc.6b00203
[34]	Cha, M.; Shoner, S. C.; Kovacs, J. A. Inorg. Chem. 1993, 32, 1860. doi: 10.1021/ic00061a052
[35]	Tzeng, Y.-L.; Yang, P.-F.; Mei, N.-W.; Yuan, T.-M.; Yu, C.-C.; Luh, T.-Y. J. Org. Chem. 1991, 56, 5289. doi: 10.1021/jo00018a016
[36]	Ni, Z.-J.; Mei, N.-W.; Shi, X.; Tzeng, Y.-L.; Wang, M. C.; Luh, T.-Y. J. Org. Chem. 1991, 56, 4035. doi: 10.1021/jo00012a043
[37]	Ananikov, V. P.; Gayduk, K. A.; Orlov, N. V.; Beletskaya, I. P.; Khrustalev, V. N.; Mikhail, Yu, A . Chem-Eur. J. 2010, 16, 2067.
[38]	Nambo, M.; Tahara, Y.; Yim, J. C.-H.; Crudden, C. M . Chem-Eur. J. 2019, 25, 1923. doi: 10.1002/chem.v25.8
[39]	Obora, Y.; Moriya, H.; Tokunaga, M.; Tsuji, Y . Chem. Commun. 2003, 22, 2820.
[40]	Leung, C. W. T.; Hong, Y.; Chen, S.; Zhao, E.; Lam, J. W. Y.; Tang, B. Z. J. Am. Chem. Soc. 2013, 135, 62. doi: 10.1021/ja310324q

Entry	Catalyst (mol%)	Ligand (mol%)	Solvent	Temp./℃	Time/h	Yield^b/% of 3a
1	NiF₂ (25)	PPh₃ (25)	THF	80	6.0	21
2	NiF₂ (25)	dppe (25)	THF	80	6.0	34
3	NiF₂ (25)	PCy₃(25)	THF	80	6.0	Trace
4	NiCl₂ (25)	dppe (25)	THF	80	6.0	38
5	NiBr₂ (25)	dppe (25)	THF	80	6.0	32
6	Ni(acac)₂ (25)	dppe (25)	THF	80	6.0	Trace
7	Ni(OAc)₂ (25)	dppe (25)	THF	80	6.0	Trace
8	NiCl₂(PPh₃)₂ (25)	dppe (25)	THF	80	6.0	25
9	NiCl₂(dppe) (25)	—	THF	80	6.0	82
10	NiCl₂(dppe) (25)	—	Toluene	80	6.0	78
11	NiCl₂(dppe) (25)	—	DCM	80	6.0	62
12	NiCl₂(dppe) (25)	—	CH₃CN	80	6.0	74
13	NiCl₂(dppe) (10)	—	THF	80	6.0	65
14	NiCl₂(dppe) (10)	—	THF	120	6.0	60
15	NiCl₂(dppe) (10)	—	THF	80	8.0	72
16	NiCl₂(dppe) (10)	—	THF	80	12	81
17	NiCl₂(dppe) (5.0)	—	THF	80	20	89 (87)^c
18	NiCl₂(dppe) (1.0)	—	THF	80	30	48
19^d	NiCl₂(dppe) (5.0)	—	THF	80	20	89

Entry	Catalyst (mol%)	Ligand (mol%)	Solvent	Temp./℃	Time/h	Yield^b/% of 3a
1	NiF₂ (25)	PPh₃ (25)	THF	80	6.0	21
2	NiF₂ (25)	dppe (25)	THF	80	6.0	34
3	NiF₂ (25)	PCy₃(25)	THF	80	6.0	Trace
4	NiCl₂ (25)	dppe (25)	THF	80	6.0	38
5	NiBr₂ (25)	dppe (25)	THF	80	6.0	32
6	Ni(acac)₂ (25)	dppe (25)	THF	80	6.0	Trace
7	Ni(OAc)₂ (25)	dppe (25)	THF	80	6.0	Trace
8	NiCl₂(PPh₃)₂ (25)	dppe (25)	THF	80	6.0	25
9	NiCl₂(dppe) (25)	—	THF	80	6.0	82
10	NiCl₂(dppe) (25)	—	Toluene	80	6.0	78
11	NiCl₂(dppe) (25)	—	DCM	80	6.0	62
12	NiCl₂(dppe) (25)	—	CH₃CN	80	6.0	74
13	NiCl₂(dppe) (10)	—	THF	80	6.0	65
14	NiCl₂(dppe) (10)	—	THF	120	6.0	60
15	NiCl₂(dppe) (10)	—	THF	80	8.0	72
16	NiCl₂(dppe) (10)	—	THF	80	12	81
17	NiCl₂(dppe) (5.0)	—	THF	80	20	89 (87)^c
18	NiCl₂(dppe) (1.0)	—	THF	80	30	48
19^d	NiCl₂(dppe) (5.0)	—	THF	80	20	89

Entry	R¹	R²	R³	X	Product	Yield^b/%
1	Ph	Ph	Me	Cl	3a	87
2	Ph	4-MeC₆H₄	Me	Cl	3b	86
3	Ph	4-MeOC₆H₄	Me	Cl	3c	85
4	Ph	4-MeC₆H₄	Et	Cl	3d	86
5	3-ClC₆H₄	Ph	Et	Cl	3e	72
6	Ph	Ph	Et	Cl	3f	88
7	Ph	Ph	Ph	Br	4b	79
8	Ph	4-MeC₆H₄	Ph	Br	4b	72
9	4-FC₆H₄	Ph	Ph	Br	4c	63
10	Ph	Ph	4-MeC₆H₄	Br	4d	80
11	Ph	4-MeC₆H₄	4-MeC₆H₄	Br	4d	84
12	Ph	Ph	2-MeOC₆H₄	Br	4e	Trace^c
13	n-Pr	Ph	Ph	Br		N.R.^d
14	Ph	n-Pr	Ph	Br		N.R.

Entry	R¹	R²	R³	X	Product	Yield^b/%
1	Ph	Ph	Me	Cl	3a	87
2	Ph	4-MeC₆H₄	Me	Cl	3b	86
3	Ph	4-MeOC₆H₄	Me	Cl	3c	85
4	Ph	4-MeC₆H₄	Et	Cl	3d	86
5	3-ClC₆H₄	Ph	Et	Cl	3e	72
6	Ph	Ph	Et	Cl	3f	88
7	Ph	Ph	Ph	Br	4b	79
8	Ph	4-MeC₆H₄	Ph	Br	4b	72
9	4-FC₆H₄	Ph	Ph	Br	4c	63
10	Ph	Ph	4-MeC₆H₄	Br	4d	80
11	Ph	4-MeC₆H₄	4-MeC₆H₄	Br	4d	84
12	Ph	Ph	2-MeOC₆H₄	Br	4e	Trace^c
13	n-Pr	Ph	Ph	Br		N.R.^d
14	Ph	n-Pr	Ph	Br		N.R.

镍催化(Z)-1,2-二芳硫基-1,2-二芳基烯烃与格氏试剂偶联反应制备多取代烯烃

Nickel-Catalyzed Coupling of 1,2-Diarylthio-1,2-diarylalkenes with Grignard Reagents for Synthesis of Multi-substituted Alkenes

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 3

References 40

Related Articles 5

Recommended Articles

Metrics

Comments

[1]	Liu Qiang, Wang Bin, Peng Xiaoshui, Wong Henry N. C.. Effects of Additives in Iron-Catalyzed Cross-Coupling Reactions Involving Grignard Reagents [J]. Chin. J. Org. Chem., 2018, 38(1): 40-50.
[2]	Chen Jinyang, Wu Xiaobo, Yi Rongnan, Xu Xinxua. Nickel-Catalyzed Coupling of Grignard Reagents and Diaryl Acetylenes for Synthesis of Tetra-substituted Naphthalenes [J]. Chin. J. Org. Chem., 2017, 37(7): 1850-1854.
[3]	Kang Juan, Huang Danfeng, Wang Kehu, Su Yingpeng, Hu Yulai, Chang Qing. Synthesis of α-Trifluoromethyl-α-hydroxyl Weinreb Amides [J]. Chin. J. Org. Chem., 2017, 37(1): 103-109.
[4]	Jia Wan, Zhao Lizhi, Wei Hengxu, Zhu Lindong, Fu Lei, Chen Weichun. Iron-Catalyzed Cross-Coupling of Secondary Alkyl Chloride and the Alkynes Grignard Reagent [J]. Chin. J. Org. Chem., 2016, 36(5): 1060-1064.
[5]	Ma Lifang, L? Wenxian, Huang Danfeng, Niu Teng, Su Yingpeng, Wang Kehu, Hu Yulai. A New Method for the Synthesis of Phenanthridine Compounds [J]. Chin. J. Org. Chem., 2014, 34(5): 962-967.