CuSO4·5H2O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes

doi:10.6023/cjoc201701013

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1855-1859.DOI: 10.6023/cjoc201701013 Previous Articles Next Articles

Notes

CuSO₄·5H₂O/NaAsc催化下碘代芳烃和末端炔烃的Sonogashira偶联反应

戚海棠, 宋光琳, 权正军, 王喜存

西北师范大学化学化工学院兰州 730070

收稿日期:2017-01-05 修回日期:2017-02-22 发布日期:2017-03-14
通讯作者: 王喜存, 权正军 E-mail:wangxicun@nwnu.edu.cn;quanzhengjun@hotmail.com
基金资助:
国家自然科学基金（Nos.21362032，21362031）资助项目.

CuSO₄·5H₂O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes

Qi Haitang, Song Guanglin, Quan Zhengjun, Wang Xicun

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2017-01-05 Revised:2017-02-22 Published:2017-03-14
Contact: 10.6023/cjoc201701013 E-mail:wangxicun@nwnu.edu.cn;quanzhengjun@hotmail.com
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21362032,21362031).

1. CuSO₄·5H₂O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes.PDF(1551KB)

Abstract

In this paper, the homogeneous catalytic system of CuSO₄·5H₂O/NaAsc was used to realize the Sonogashira reaction of aryl iodides and terminal alkynes. This catalytic system replaces the general catalytic system of Pd/Cu-bound phosphorus ligand, which has the advantages of cheap catalyst, simple post-treatment, reaction under homogeneous conditions, and meets the requirements of green chemistry.

Key words: aryl iodides, terminal alkynes, CuSO₄·, 5H₂O/NaAsc, Sonogashira coupling

Cite this article

Qi Haitang, Song Guanglin, Quan Zhengjun, Wang Xicun. CuSO₄·5H₂O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes[J]. Chin. J. Org. Chem., 2017, 37(7): 1855-1859.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Diek, H. A.; Heck, F. R. J. Organomet. Chem. 1975, 93, 259.
[2] Cassar, L. J. Organomet. Chem. 1975, 93, 253.
[3] Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
[4] (a) Wang, D.; Gao, S. H. Org. Chem. Front. 2014, 1, 556.
(b) Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem., Int. Ed. 2001, 40, 603.
(c) Paterson, I.; Paquet, T. Org. Lett. 2010, 12, 2158.
(d) Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378.
(e) Myers, A. G.; Hogan, P. C.; Hurd, A. R.; Goldberg, S. D. Angew. Chem., Int. Ed. 2002, 41, 1062。
(f) Koyama, Y.; Lear, M. J.; Mashimo, T.; Hirama, M. Org. Lett. 2005, 7, 267.
[5] (a) Erdélyi, M.; Gogoll, A. J. Org. Chem. 2003, 68, 6431.
(b) Elangovan, A.; Wang, Y. H.; Ho, T. I. Org. Lett. 2003, 5, 1841.
(c) Cranwell, P. B.; Peterson, A. M.; Littlefield, B. T. R.; Russell, A.T. J. Chem. Ed. 2015, 92, 1110.
[6] Wen, T. M.; Xie, J. Y.; Feng, R. G.; Huang, X. M. Chin. J. Org. Chem. 2015, 35, 735(in Chinese). (温燕梅, 谢建英, 冯润光, 黄绪明, 有机化学, 2015, 35, 735.)
[7] García, D.; Cuadro, A. M.; Builla, J. A.; Vaquero, J. J. Org. Lett. 2004, 6, 4175.
[8] Bakherad, M. Appl. Organomet. Chem. 2013, 27, 125.
[9] Christopher, W.; Gallop, D.; Chen, M. T.; Navarro, O. Org. Lett. 2014, 16, 3724.
[10] (a) Xu, W.; Sun, H. M.; Yu, B.; Zhang, G. F.; Zhang, W. Q.; Gao, Z. W. Appl. Mater. Interf. 2014, 6, 20261.
(b) Diyarbakir, S.; Can, H.; Metin, O. Appl. Mater. Interf. 2015, 7, 3199.
[11] Ren, X.; Kong, S.; Shu, Q.; Shu, M. Chin. J. Chem. 2016, 34, 373.
[12] Sikk, L.; Taul, J. T.; Burk, P. Organometallics 2011, 30, 5656.
[13] (a) Prabhu, R. N.; Pal, S. Tetrahedron Lett. 2015, 56, 5252.
(b) Huang, H.; Liu, H.; Jiang, H. L.; Chen, K. X. J. Org. Chem. 2008, 73, 6037.
(c) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691.
[14] Carnavalet, B. D. C.; Archambeau, A.; Meyer, C.; Cossy, J.; Folléas, B.; Brayer, J. L.; Demoute, J. P. Org. Lett. 2011, 13, 956.
[15] Zhang, G.; Zhang, W.; Luan, Y.; Han, X.; Ding C. Chin. J. Chem. 2015, 33, 705.
[16] (a) Hu, H.; Yang, F.; Wu, Y. J. J. Org. Chem. 2013, 78, 10506.
(b) Liang, B.; Dai, M. J.; Chen, J. H.; Yang, Z. J. Org. Chem. 2005, 70, 391.
(c) Gogoi, A.; Dewana, A.; Bora, U. RSC Adv. 2015, 5, 16.
(d) Liang, Y.; Xie, Y. X.; Li, J. H. J. Org. Chem. 2006, 71, 379.
(e) Pu, X. T.; Li, H. B.; Colacot, T. J. J. Org. Chem. 2013, 78, 568.
(f) Pérez, A. L.; Meseguer, J. O.; Marqués, P. R.; Corma, A. Angew. Chem., Int. Ed. 2013, 52, 11554.
[17] Lauterbach, T.; Livendahl, M.; Rosellón, A; Espinet, P.; Echavarren, A. M. Org. Lett. 2010, 12, 3006.
[18] Okuro, K.; Furuune, M.; Enna, M.; Miura, M.; Nomura, M. J. Org. Chem. 1993, 58, 4716.
[19] (a) Lin, C. H.; Wang, Y. J.; Lee, C. F. Eur. J. Org. Chem. 2010, 4368.
(b) Kotovshchikov, Y. N.; Latyshev, G. V.; Lukashev, N. V.; Beletskaya, I. P. Org. Biomol. Chem. 2015, 13, 5542.
(c) Bates, C. G.; Saejueng, P.; Venkataraman, D. Org. Lett. 2004, 6, 1441.
(d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.
[20] (a) Ma, D. W.; Liu, F. Chem. Commun. 2004, 1934.
(b) Liu, F.; Ma, D. W. J. Org. Chem. 2007, 72, 4844.
(c) Santandrea, J.; Bédard, A. C.; Collins, S. K. Org. Lett. 2014, 16, 3892.
[21] Wu, M. Y.; Mao, J. C.; Guo, J.; Ji, S. J. Eur. J. Org. Chem. 2008, 4050.
[22] (a) Messeguer, J. O.; Liu, L.; García, S. G.; Giménez, C. C.; Domínguez, I.; Gavara, R.; Carbó, A. D.; Concepción, P.; Pérez, A. L.; Corma, A. J. Am. Chem. Soc. 2015, 137, 3894.
[23] He, H.; Wu, Y. J. Tetrahedron Lett. 2004, 45, 3237.
[24] Monnier,F.; Turtaut, F.; Duroure, L.; Taillefer, M. Org. Lett. 2008, 10, 3203.
(b) Nakane, T.; Tanioka, Y.; Tsukada, N. Organometallics 2015, 34, 1191.
[25] Carril, M.; Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 4862.
[26] (a) Wang, M.; Li, P. H.; Wang, L. Synth. Commun. 2004, 34, 2803.
(b) Wang, L.; Li, P. H.; Zhang, Y. C. Chem. Commun. 2004, 514.
[27] (a) Quan, Z. J.; Xu, Q.; Zhang, Z.; Da, Y. X.; Wang, X. C. Tetrahedron 2013, 69, 881.
(b) Quan, Z. J.; Xia, H. D.; Zhang, Z.; Da, Y. X.; Wang, X. C. Tetrahedron 2013, 69, 8368.
(c) Quan, Z. J.; Xia, H. D.; Zhang, Z.; Da, Y. X.; Wang, X. C. Chin. J. Chem. 2013, 31, 501.
(d) Song, G. L.; Zhang, Z.; Da, Y. X.; Wang, X. C. Tetrahedron 2015, 71, 8823.
[28] (a) Kuhn, P.; Alix, A.; Kumarraja, M.; Louis, B.; Pale, P.; Sommer, J. Eur. J. Org. Chem. 2009, 423.
(b) Peng, H. H; Xi, Y. M.; Ronaghi, N.; Dong, B.; Akhmedov, N. G.; Shi, X. D. J. Am. Chem. Soc. 2014, 136, 13174.
(c) Weng, Y.; Cheng, B.; He, C.; Lei, A. W. Angew. Chem., Int. Ed. 2012, 51, 9547.
[29] (a) Wu, M. Y.; Mao, J. C.; Guo, J.; Jun, S. Eur. J. Org. Chem. 2008, 4050.
(b) Gujadhur, R. K. Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.
[30] Magagnano, G.; Gualandi, A.; Marchini, M.; Mengozzi, L.; Ceroni, P.; Cozzi, P. G. Chem. Commun. 2017, 53, 1591.

CuSO₄·5H₂O/NaAsc催化下碘代芳烃和末端炔烃的Sonogashira偶联反应

CuSO₄·5H₂O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 7

Recommended Articles

Metrics

Comments

[1]	Chunming Gui, Tongyao Zhou, Haifeng Wang, Qiongjiao Yan, Wei Wang, Jin Huang, Fener Chen. Recent Advances in Visible Light Photoredox-Catalyzed Alkynylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2647-2663.
[2]	Hu Zhifang, Peng Lifen, Qiu Renhua, Orita Akihiro. Recent Progress of Protecting Groups for Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3112-3119.
[3]	Ma Nan, Zeng Xianghua. Cu₂O-Catalyzed Green Oxidative Terminal Alkynes Homocoupling without Bases [J]. Chin. J. Org. Chem., 2018, 38(6): 1556-1561.
[4]	Kong Shengnan, Malik Abaid Ullah, Qian Xuefeng, Shu Mouhai, Xiao Wende. C-C Coupling Reactions in Water Catalyzed by Palladium [J]. Chin. J. Org. Chem., 2018, 38(2): 432-442.
[5]	Yuan Hang, Chen Huilian, Luo Zhibin, Gao Yuhua, Lu Hongfei. Synthesis of a Pd-Pyridine N-Heterocyclic Carbene Complex (NHC)-PdCl₂(Py) and Its Efficient Application in Coupling Reaction [J]. Chin. J. Org. Chem., 2017, 37(11): 2948-2955.
[6]	Wang Chao, Deng Nan, Wang Lingling, Xu Dingjian, Yao Xiaoquan. Cu-Ag Bimetallic Nanoparticles Catalyzed Addition of Terminal Alkynes to Aldehydes [J]. Chin. J. Org. Chem., 2016, 36(5): 1034-1043.
[7]	JI Xian-Yong, ZHANG Jing, TANG Can-Lin, WANG Jie. Synthesis and Optical Properties of Unsymmetrical Conjugated Den-drons Terminated with Isophthalate Ester [J]. Chin. J. Org. Chem., 2011, 31(01): 126-131.

CuSO4·5H2O/NaAsc催化下碘代芳烃和末端炔烃的Sonogashira偶联反应