Palladium-Catalyzed Cross-Coupling Reaction of Arenesulphonate with Phosphite

doi:10.6023/cjoc201710031

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (4): 896-901.DOI: 10.6023/cjoc201710031 Previous Articles Next Articles

Articles

钯催化芳基磺酸酯与亚磷酸酯的交叉偶联反应

冯志刚^a, 谢小敏^b, 张兆国^a,b

a 上海应用技术大学化学与环境工程学院上海 201418;
b 上海交通大学化学化工学院上海 200240

收稿日期:2017-10-24 修回日期:2017-11-18 发布日期:2017-12-05
通讯作者: 张兆国 E-mail:zhaoguo@sjtu.edu.cn
基金资助:
国家自然科学基金（No.21472124）资助项目.

Palladium-Catalyzed Cross-Coupling Reaction of Arenesulphonate with Phosphite

Feng Zhigang^a, Xie Xiaomin^b, Zhang Zhaoguo^a,b

a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240

Received:2017-10-24 Revised:2017-11-18 Published:2017-12-05
Contact: 10.6023/cjoc201710031 E-mail:zhaoguo@sjtu.edu.cn
Supported by:
Project supported by the National Natural Sciences Foundation of China (No. 21472124).

1. Palladium-Catalyzed Cross-Coupling Reaction of Arenesulphonate with Phosphite.PDF(1553KB)

Abstract

Organo-phosphorus compounds have important applications in metal-organic chemistry, coordination chemistry and biochemistry. Therefore, the C-P cross-coupling reaction was an important method to prepare organo-phosphorus, which is also a hotspot of current research. Hence, we have studied a kind of cross-coupling reaction between arenesulphonate and phosphites using palladium as the catalyst to synthesize a series of organo-phosphorus compounds efficiently, and the approach was applied to prepare a chiral N/P ligand.

Key words: arenesulphonate, phosphite, palladium, cross-coupling

Cite this article

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.

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[1] (a) Hostetler, K. Y. Antiviral Res. 2009, 82, A84.
(b) Thornton, P. J.; Kadri, H.; Miccoli, A.; Mehellou, Y. J. Med. Chem. 2016, 59, 10400.
(c) Wagner, C. R.; Iyer, V. V.; McIntee, E. J. Med. Res. Rev. 2000, 20, 417.
[2] (a) Fu, W.; Tang, W. ACS Catal. 2016, 6, 4814.
(b) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
[3] (a) Zhang, Y.; Yue, B.; Han, S.; Yan, L. RSC Adv. 2014, 4, 33702.
(b) Morisaki, Y.; Ouchi, Y.; Fukui, T.; Naka, K.; Chujo, Y. Tetrahedron Lett. 2005, 46, 7011.
[4] (a) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
(b) Fandrick, K. R.; Fandrick, D. R.; Reeves, J. T.; Gao, J.; Ma, S.; Li, W.; Lee, H.; Grinberg, N.; Lu, B.; Senanayake, C. H. J. Am. Chem. Soc. 2011, 133, 10332.
(c) Lu, B.; Wang, Q.; Zhao, M.; Xie, X.; Zhang, Z. J. Org. Chem. 2015, 80, 9563.
[5] Berthod, M.; Mignani, G.; Woodward, G.; Lemaire, M. Chem. Rev. 2005, 105, 1801.
[6] (a) Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170.
(b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
(c) Lee, C. K.; Shin, S. R.; Mun, J. Y.; Han, S.-S.; So, I.; Jeon, J.-H.; Kang, T. M.; Kim, S. I.; Whitten, P. G.; Wallace, G. G.; Spinks, G. M.; Kim, S. J. Angew. Chem., Int. Ed. 2009, 48, 5116.
(d) Shi, Y.; Peterson, S. M.; Haberaecker, W. W.; Blum, S. A. J. Am. Chem. Soc. 2008, 130, 2168.
(e) Shen, X.; Jones, G. O.; Watson, D. A.; Bhayana, B.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 11278.
(f) Sase, S.; Jaric, M.; Metzger, A.; Malakhov, V.; Knochel, P. J. Org. Chem. 2008, 73, 7380.
[7] (a) Kalek, M.; Jezowska, M.; Stawinski, J. Adv. Synth. Catal. 2009, 351, 3207.
(b) Wang, T.; Sang, S.; Liu, L.; Qiao, H.; Gao, Y.; Zhao, Y. J. Org. Chem. 2014, 79, 608.
(c) Hong, G.; Mao, D.; Wu, S.; Wang, L. J. Org. Chem. 2014, 79, 10629.
(d) Deal, E. L.; Petit, C.; Montchamp, J.-L. Org. Lett. 2011, 13, 3270.
(e) Bloomfield, A. J.; Herzon, S. B. Org. Lett. 2012, 14, 4370.
(f) Zhu, J.; Mao, M.; Ji, H.-J.; Xu, J.-Y.; Wu, L. Org. Lett. 2017, 19, 1946.
[8] (a) Gao, Y.; Wang, G.; Chen, L.; Xu, P.; Zhao, Y.; Zhou, Y.; Han, L.-B. J. Am. Chem. Soc. 2009, 131, 7956.
(b) Huang, C.; Tang, X.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2006, 71, 5020.
(c) Zhang, H.; Li, W.; Zhu, C. J. Org. Chem. 2017, 82, 2199.
(d) Thielges, S.; Bisseret, P.; Eustache, J. Org. Lett. 2005, 7, 681.
(e) Hu, G.; Shan, C.; Chen, W.; Xu, P.; Gao, Y.; Zhao, Y. Org. Lett. 2016, 18, 6066.
(f) Xu, Q.; Jia, X.; Li, X.; Sun, Q.; Zhou, Y.; Yin, S.; Han, L. Chin. J. Org. Chem. 2014, 34, 1340(in Chinese). (徐清, 贾晓娟, 李晓慧, 孙清, 周永波, 尹双凤, 韩立彪, 有机化学, 2014, 34, 1340.)
(g) Xu, Q.; Zhao, C.; Zhou, Y.; Yin, S.; Han, L. Chin. J. Org. Chem. 2012, 32, 1761(in Chinese). (徐清, 赵长秋, 周永波, 尹双凤, 韩立彪, 有机化学, 2012, 32, 1761.)
(h) Zhang, Y.; Wang, M.; Cao, P.; Liao, J. Acta Chim. Sinica 2017, 75, 794(in Chinese). (张涌灵, 王敏, 曹鹏, 廖健, 化学学报, 2017, 75, 794.)
[9] (a) Shen, C.; Yang, G.; Zhang, W. Org. Biomol. Chem. 2012, 10, 3500.
(b) Wu, Y.; Liu, L.; Yan, K.; Xu, P.; Gao, Y.; Zhao, Y. J. Org. Chem. 2014, 79, 8118.
(c) Zhang, X.; Liu, H.; Hu, X.; Tang, G.; Zhu, J.; Zhao, Y. Org. Lett. 2011, 13, 3478.
(d) Zhao, Y.-L.; Wu, G.-J.; Han, F.-S. Chem. Commun. 2012, 48, 5868.
[10] (a) Kagayama, T.; Nakano, A.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2006, 8, 407.
(b) Mu, X.-J.; Zou, J.-P.; Qian, Q.-F.; Zhang, W. Org. Lett. 2006, 8, 5291.
(c) Pan, X.-Q.; Zou, J.-P.; Zhang, G.-L.; Zhang, W. Chem. Commun. 2010, 46, 1721.
(d) Xu, W.; Zou, J.-P.; Zhang, W. Tetrahedron Lett. 2010, 51, 2639.
[11] (a) Xiang, C.-B.; Bian, Y.-J.; Mao, X.-R.; Huang, Z.-Z. J. Org. Chem. 2012, 77, 7706.
(b) Hu, G.; Chen, W.; Ma, D.; Zhang, Y.; Xu, P.; Gao, Y.; Zhao, Y. J. Org. Chem. 2016, 81, 1704.
(c) Zhang, H.; Gu, Z.; Li, Z.; Pan, C.; Li, W.; Hu, H.; Zhu, C. J. Org. Chem. 2016, 81, 2122.
(d) Hu, G.; Chen, W.; Ma, D.; Zhang, Y.; Xu, P.; Gao, Y.; Zhao, Y. J. Org. Chem. 2016, 81, 2680.
(e) Zhang, B.; Daniliuc, C. G.; Studer, A. Org. Lett. 2014, 16, 250.
[12] Zhao, Q.-Y.; Shi, M. Tetrahedron 2011, 67, 3724.
[13] (a) Naud, F.; Malan, C.; Spindler, F.; Rüggeberg, C.; Schmidt, A. T.; Blaser, H.-U. Adv. Synth. Catal. 2006, 348, 47.
(b) Tellers, D. M.; Bio, M.; Song, Z. J.; McWilliams, J. C.; Sun, Y. Tetrahedron:Asymmetry 2006, 17, 550.
[14] (a) Liu, D.; Xie, F.; Zhao, X.; Zhang, W. Tetrahedron 2008, 64, 3561.
(b) Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics 1999, 18, 2291.
[15] (a) Coyne, A. G.; Guiry, P. J. Tetrahedron Lett. 2007, 48, 747.
(b) Nishibayashi, Y.; Takei, I.; Uemura, S.; Hidai, M. Organometallics 1998, 17, 3420.
[16] (a) Fukuzumi, T.; Shibata, N.; Sugiura, M.; Yasui, H.; Nakamura, S.; Toru, T. Angew. Chem., Int. Ed. 2006, 45, 4973.
(b) Lu, Z.; Ma, S. Angew. Chem., Int. Ed. 2008, 47, 258.
(c) Nemoto, T.; Masuda, T.; Matsumoto, T.; Hamada, Y. J. Org. Chem. 2005, 70, 7172.
(d) Hou, X.-L.; Sun, N. Org. Lett. 2004, 6, 4399.
(e) Nemoto, T.; Masuda, T.; Akimoto, Y.; Fukuyama, T.; Hamada, Y. Org. Lett. 2005, 7, 4447.
[17] Procter, D. J.; Rayner, C. M. Synth. Commun. 2000, 30, 2975.
[18] Deng, H.-P.; Wei, Y.; Shi, M. Adv. Synth. Catal. 2009, 351, 2897.

钯催化芳基磺酸酯与亚磷酸酯的交叉偶联反应

Palladium-Catalyzed Cross-Coupling Reaction of Arenesulphonate with Phosphite

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