Recent Advances in the Synthesis of Organophosphorus Compounds via Cross Coupling between Readily Available Materials and P-H Compounds

doi:10.6023/cjoc201702050

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1055-1068.DOI: 10.6023/cjoc201702050 Previous Articles Next Articles

REVIEW

简单易得试剂与磷-氢化合物交叉偶联合成有机磷化合物

杨佳^a, 肖晶^a,c, 周永波^a, 陈铁桥^a, 尹双凤^a, 韩立彪^b

a 湖南大学化学化工学院化学生物传感与计量学国家重点实验室长沙 410082;
b National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan;
c 湖南科技大学理论有机化学与功能分子教育部重点实验室湘潭 411201

收稿日期:2017-02-28 修回日期:2017-04-08 发布日期:2017-05-02
通讯作者: 周永波,韩立彪 E-mail:zhouyb@hnu.edu.cn;libiao-han@aist.go.jp
基金资助:
国家自然科学基金（Nos.21373080，21573065，21273066）和湖南省杰出青年基金（No.2016JJ1007）资助项目.

Recent Advances in the Synthesis of Organophosphorus Compounds via Cross Coupling between Readily Available Materials and P-H Compounds

Yang Jia^a, Xiao Jing^a,c, Zhou Yongbo^a, Chen Tieqiao^a, Yin Shuangfeng^a, Han Libiao^b

a State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
b National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan;
c Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of the Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201

Received:2017-02-28 Revised:2017-04-08 Published:2017-05-02
Contact: 10.6023/cjoc201702050 E-mail:zhouyb@hnu.edu.cn;libiao-han@aist.go.jp
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21373080, 21573065, 21273066), and the Natural Science Foundation of Hunan Province (No. 2016JJ1007)

This mini-review focuses on the recent advances in the synthesis of organophosphorus compounds via cross coupling of P-H compounds with readily available starting materials, mainly including the reactions of terminal alkynes and heteroatom compounds (oxygen, sulfur or nitrogen-contained compounds) with P-H compounds forming sp-C-P, sp²-C-P, sp³-C-P, and P-Z bonds. Related reaction mechanisms are also discussed.

Key words: P-H compounds, cross coupling, organophosphorus compounds

Cite this article

Yang Jia, Xiao Jing, Zhou Yongbo, Chen Tieqiao, Yin Shuangfeng, Han Libiao. Recent Advances in the Synthesis of Organophosphorus Compounds via Cross Coupling between Readily Available Materials and P-H Compounds[J]. Chin. J. Org. Chem., 2017, 37(5): 1055-1068.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Quin, L. D. A Guide to Organophosphorus Chemistry, Wiley Interscience. New York, 2000.
(b) Majoral, J.-P. New Aspects in Phosphorus Chemistry, Springer, Berlin, Germany, Vol. 1～5, 2002～2005.
(c) Murphy, P. J. Organophosphorus Reagents, Oxford University Press, Oxford, U. K., 2004.
(d) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
(e) Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681.
(f) Queffélec, C.; Petit, M.; Janvier, P.; Knight, D. A.; Bujoli, B. Chem. Rev. 2012, 112, 3777.
(g) Yang, L.; Ma J. Acta Chim. Sinica 2016, 74, 130 (in Chinese). (杨丽军, 马军安, 化学学报, 2016, 74, 130.)
(h) Shi, B.; Fang, Y.; Zhang, L.; Jin, X.; Wu, Y.; Fang, M.; Yang, Y.; Chen, C. Chin. J. Org. Chem. 2016, 36, 673 (in Chinese). (施波超, 方烨汶, 张莉, 金小平, 武永辉, 方媚, 杨宇飞, 陈冲, 有机化学, 2016, 36, 673.)
(i) Jin, C.; He, J.; Wang, C.; He, H. Chin. J. Org. Chem. 2010, 30, 1 (in Chinese). (金传飞, 贺军波, 王储备, 贺红武, 有机化学, 2010, 30, 1.)
(j) Zhao, Y.; Xiao, Q.; Ju, Y.; Li, Y. Chin. J. Org. Chem. 2001, 21, 869 (in Chinese). (赵玉芬, 肖强, 巨勇, 李艳梅, 有机化学, 2001, 21, 869.)
[2] (a) Engel, R. Handbook of Organophosphorus Chemistry, Marcel Dekker, New York, 1998.
(b) Jiménez, M. V.; Pérez-Torrente, J. J.; Bartolomé, M. I.; Oro, L. A. Synthesis 2009, 1916.
(c) Casey, C. P.; Paulsen, E. L.; Beuttenmueller, E. W.; Proft, B. R.; Petrovich, L. M.; Matter, B. A.; Powell, D. R. J. Am. Chem. Soc. 1997, 119, 11817.
(d) Kinas, R. W.; Okruszek, A.; Stec, W. J. Tetrahedron Lett. 2002, 43, 7875.
[3] (a) Tappe, F. M. J.; Trepohl, V. T.; Oestreich, M. Synthesis 2010, 3037.
(b) Chen, T.; Zhang, J.-S.; Han, L.-B. Dalton Trans. 2016, 45, 1843.
(c) Jablonkai, E.; Keglevich, G. Curr. Org. Synth. 2014, 11, 429.
(d) Shao, C.; Xu, W.; Li, L.; Zhang, X.. Chin. J. Org. Chem. 2017, 37, 335 (in Chinese). (邵长伟, 徐炜刚, 李亮, 张兴华, 有机化学, 2017, 37, 335.)
(e) Zhang, L.; Zhang, P.; Xue, J.; Sun, W.; Zou, J. Acta Chim. Sinica 2016, 74, 811 (in Chinese). (张令, 张沛之, 薛剑飞, 孙网彬, 邹建平, 化学学报, 2016, 74, 811.)
(f) Xu, Q.; Jia, X.; Li, X.; Sun, Q.; Zhou, Y.-B.; Yin, S.-F.; Han, L.-B. Chin. J. Org. Chem. 2014, 34, 1340 (in Chinese). (徐清, 贾小娟, 李晓慧, 孙清, 周永波, 尹双凤, 韩立彪, 有机化学, 2014, 34, 1340.)
[4] (a) Mo, J.; Kang, D.; Eom, D.; Kim, S. H.; Lee, P. H. Org. Lett. 2013, 15, 26.
(b) Li, X.; Hu, G.; Luo, P.; Tang, G.; Gao, Y.; Xu, P.; Zhao, Y. Adv. Synth. Catal. 2012, 354, 2427.
(c) Ekkert, O.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc. 2011, 133, 4610.
(d) Van derpoorten, K.; Migaud, M. E. Org. Lett. 2004, 6, 3461.
[5] Iorga, B.; Eymery, F.; Carmichael, D.; Savignac, P. Eur. J. Org. Chem. 2000, 65, 3103 and references cited therein.
[6] (a) Girard, S. A.; Knauber, T.; Li, C.-J. Angew. Chem., Int. Ed. 2014, 53, 74.
(b) Waterman, R. Chem. Soc. Rev. 2013, 42, 5629.
(c) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(d) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
(e) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293.
[7] Gao, Y.; Wang, G.; Chen, L.; Xu, P.; Zhao, Y.; Zhou, Y.; Han, L.-B. J. Am. Chem. Soc. 2009, 131, 7956.
[8] (a) Yang, J.; Chen, T.; Zhou, Y.; Yin, S.; Han, L.-B. Chem. Commun. 2015, 51, 3549.
(b) Yang, J.; Chen, T.; Zhou, Y.; Yin, S.-F.; Han, L.-B. Organometallics 2015, 34, 5095.
[9] Wang, T.; Chen, S.; Shao, A.; Gao, M.; Huang, Y.; Lei, A. Org. Lett. 2015, 17, 118.
[10] (a) Bhattachary, A. K.; Thyarajan, G. Chem. Rev. 1981, 81, 415.
(b) Yang, G.; Shen, C.; Zhang, L.; Zhang, W. Tetrahedron Lett. 2011, 52, 5032.
(c) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1980, 21, 3595.
(d) Berger, O.; Petit, C.; Deal, E. L.; Montchamp, J.-L. Adv. Synth. Catal. 2013, 355, 1361.
[11] Reviews for C-O bond activation, see: (a) Tobisu, M.; Chatani, N. Acc. Chem. Res. 2015, 48, 1717.
(b) Chen, T.; Han, L.-B. Angew. Chem., Int. Ed. 2015, 54, 8600.
(c) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509. 299.
(d) Cornella, J.; Zarate, C.; Martin, R. Chem. Soc. Rev. 2014, 43, 8081.
[12] Zhao, Y.-L.; Wu, G.-J.; Han, F.-S. Chem. Commun. 2012, 48, 5868.
[13] Shen, C.; Yang, G.; Zhang, W. Org. Biomol. Chem. 2012, 10, 3500.
[14] Fu, W. C.; So, C. M.; Kwong, F. Y. Org. Lett. 2015, 17, 5906.
[15] Yang, J.; Chen, T.; Han, L.-B. J. Am. Chem. Soc. 2015, 137, 1782.
[16] Yang, J.; Xiao, J.; Chen, T.; Han, L.-B. J. Org. Chem. 2016, 81, 3911.
[17] Yang, J.; Xiao, J.; Chen, T.; Han, L.-B. J. Organomet. Chem. 2016, 820, 120.
[18] Li, X.; Chen, T.; Saga, Y.; Han, L.-B. Dalton Trans. 2016, 45, 1877.
[19] (a) Steinbach, T.; Wurm, F. R. Angew. Chem., Int. Ed. 2015, 54, 6098.
(b) Bogomilova, A.; Hohn, M.; Gunther, M.; Troev, K.; Wagner, E.; Schreiner, L. Eur. J. Pharm. Sci. 2013, 50, 410.
(c) Rectenwald, M. F.; Gaffen, J. R.; Rheingold, A. L.; Morgan A. B.; Protasiewicz, J. D. Angew. Chem., Int. Ed. 2014, 53, 4173.
[20] (a) Oliana, M.; King, F.; Horton, P. N.; Hursthouse, M. B.; Hii, K. K. J. Org. Chem. 2006, 71, 2472.
(b) Zhou, Y.; Wang, G.; Saga, Y.; Shen, R.; Goto, M.; Zhao, Y.; Han, L.-B. J. Org. Chem. 2010, 75, 7924.
(c) Wang, G.; Shen, R.; Xu, Q.; Goto, M.; Zhao, Y.; Han, L.-B. J. Org. Chem. 2010, 75, 3890.
[21] Dhineshkumar, J.; Prabhu, K. R. Org. Lett. 2013, 15, 6062.
[22] Li, S.; Chen, T.; Saga, Y.; Han, L.-B. RSC Adv. 2015, 5, 71544.
[23] Li, C.; Chen, T.; Han, L.-B. Dalton Trans. 2016, 45, 14893.
[24] Recent reviews on metal-catalyzed C-S transformation: (a) Pan, F.; Shi, Z.-J. ACS Catal. 2014, 4, 280.
(b) Wang, L.; He, W.; Yu, Z. Chem. Soc. Rev. 2013, 42, 599.
(c) Modha, S. G.; Mehta, V. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2013, 42, 5042.
[25] Miao, T.; Wang, L. Adv. Synth. Catal. 2014, 356, 967.
[26] Li, J.; Bi, X.; Wang, H.; Xiao, J. RSC Adv. 2014, 4, 19214.
[27] Yang, J.; Xiao, J.; Chen, T.; Yin, S.-F.; Han, L.-B. Chem. Commun. 2016, 52, 12233.
[28] (a) 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.
(b) Lauer, A. M.; Mahmud, F.; Wu, J. J. Am. Chem. Soc. 2011, 133, 9119.
(c) Lauer, A. M.; Wu, J. Org. Lett. 2012, 14, 5138.
[29] (a) Atherton, F. R.; Todd, A. R. J. Chem. Soc. 1947, 674.
(b) Xiong, B.; Zhou, Y.; Zhao, C.; Goto, M.; Yin, S.-F.; Han, L.-B. Tetrahedron 2013, 69, 9373.
[30] Wang, J.; Huang, X.; Ni, Z.; Wang, S.; Wu, J.; Pan, Y. Green Chem. 2015, 17, 314.
[31] Bi, X.; Li, J.; Meng, F.; Wang, H.; Xiao, J. Tetrahedron 2016, 72, 706.
[32] Zhu, Y.; Chen, T.; Li, S.; Shimada, S.; Han, L.-B. J. Am. Chem. Soc. 2016, 138, 5825.
[33] Sun, J.-G.; Yang, H.; Li, P.; Zhang, B. Org. Lett. 2016, 18, 5114.
[34] Sun, J.-G.; Weng, W.-Z.; Li, P.; Zhang, B. Green Chem. 2017, 19, 1128.
[35] Song, S.; Zhang, Y.; Yeerlan, A.; Zhu, B.; Liu, J.; Jiao, N. Angew. Chem., Int. Ed. 2017, 56, 2487.
[36] Moon, Y.; Moon, Y.; Choi, H.; Hong, S. Green Chem. 2017, 19, 1005.
[37] Lin, Y.-M.; Lu, G.-P.; Wang, G.-X.; Yi, W.-B. J. Org. Chem. 2017, 82, 382.
[38] Ouyang, Y.-J.; Li, Y.-Y.; Li, N.-B.; Xu, X.-H. Chin. Chem. Lett. 2013, 24, 1103.
[39] Xia, M.; Chen, J. Tetrahedron Lett. 2016, 57, 4702.
[40] Li, J.; Bi, X.; Wang, H.; Xiao, J. Asian J. Org. Chem. 2014, 3, 1113.
[41] Xu, W.; Hu, G.; Xu, P.; Gao, Y.; Yin, Y.; Zhao, Y. Adv. Synth. Catal. 2014, 356, 2948.
[42] Zhang, J.-S.; Chen, T.; Yang, J.; Han, L.-B. Chem. Commun. 2015, 51, 7540.
[43] Yang, D.; Zhao, D.; Mao, L.; Wang, L.; Wang, R. J. Org. Chem. 2011, 76, 6426.
[44] Zhao, Y.; Chen, X.; Chen, T.; Zhou, Y.; Yin, S.-F.; Han, L.-B. J. Org. Chem. 2015, 80, 62.
[45] (a) Darcel, C.; Uziel, J.; Jugé, S. In Phosphorous Ligands in Asymmetric Catalysis, Ed.: Börner, A., Wiley-VCH, Weinheim, 2008, Vol. 3, p. 1211.
(b) Sawa, M.; Tsukamoto, T.; Kiyoi, T.; Kurokawa, K.; Nakajima, F.; Nakada, Y.; Yokota, K.; Inoue, Y.; Kondo, H.; Yoshino, K. J. Med. Chem. 2002, 45, 930.
(c) Moonen, K.; Laureyn, I.; Stevens, C. V. Chem. Rev. 2004, 104, 6177.
[46] Atherton, F.; Openshaw, A.; Todd, A. J. Chem. Soc. 1945, 660.
[47] Wang, G.; Yu, Q.-Y.; Chen, S.-Y.; Yu, X.-Q. Tetrahedron Lett. 2013, 54, 6230.
[48] Fraser, J.; Wilson, L. J.; Blundell, R. K.; Hayes, C. J. Chem. Commun. 2013, 49, 8919.
[49] Zhou, Y.; Yang, J.; Chen, T.; Yin, S.-F.; Han, L.-B. Bull. Chem. Soc. Jpn. 2014, 87, 400.

简单易得试剂与磷-氢化合物交叉偶联合成有机磷化合物

Recent Advances in the Synthesis of Organophosphorus Compounds via Cross Coupling between Readily Available Materials and P-H Compounds

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.
[2]	Siqiang Fang, Zanjiao Liu, Tianli Wang. Recent Advances of the Atherton-Todd Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1069-1083.
[3]	Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.
[4]	Zhaoxin Wei, Renjie Wang, Yonghong Zhang, Bin Wang, Yu Xia, Weiwei Jin, Chenjiang Liu. Electrochemical Synthesis of N-Acyl/Sulfonylsulfenamides Using Potassium Iodide as Mediator [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3730-3739.
[5]	Li Huaigui, Yang Peng, Xu Zheng, Du Zhengyin, Fu Ying. Cu-Catalyzed Direct Arylation of Benzothiazoles with Diaryliodonium Salts [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2476-2482.
[6]	Ma Xiantao, Yu Jing, Ma Ruitian, Yan Ran, Zhang Zhenlei. Palladium-Catalyzed Dehydrative Cross Couplings of Stabilized Phosphorus Ylides with Allylic Alcohols [J]. Chin. J. Org. Chem., 2019, 39(3): 830-835.
[7]	Zhao Ming, Ji Yuan. Progress on Synthetic Applications of 1,1-Dibromo-1-alkenes [J]. Chin. J. Org. Chem., 2018, 38(2): 401-415.
[8]	Wang Fan, Hu Yucai, Shen An, Cao Yucai. Novel Pd-N-Heterocyclic Carbene Complexes: Design, Synthesis and Applyment in Buchwald-Hartwig Cross Coupling Reaction [J]. Chin. J. Org. Chem., 2017, 37(8): 2050-2056.
[9]	Du Lijuan, Wu Caihong, Gu Honghong, Li Juan. A Density Functional Theory Study of the Mechanism of Cu(II)-Catalyzed Synthesis of Pyrido[1,2-a]benzimidazoles [J]. Chin. J. Org. Chem., 2015, 35(8): 1726-1732.
[10]	Jian Yong, Li Gang, Yang Peng, Deng Tuo, Zhou Xue, Xu Haiyan . Syntheses, Spectral Properties of Novel Carbazole Derivatives and Evaluations of Its Ct-DNA Interaction [J]. Chin. J. Org. Chem., 2014, 34(4): 809-816.
[11]	Wang Biyu, Ni Peizhong, Fan Jili, Zheng Huidong, Zhao Suying, Bai Zhengshuai. Pd-Complex Catalyzed Suzuki Cross-Coupling Reaction of Brominated Salicylaldehyde with Pyridylboronic Acid [J]. Chin. J. Org. Chem., 2014, 34(12): 2471-2477.
[12]	Yu Haizhu, Su Shengqin, Zhang Chi, Dang Zhi-Min. Recent Progress in Copper Catalyzed C—H Functionalizations [J]. Chin. J. Org. Chem., 2013, 33(08): 1628-1646.
[13]	Ran Longfei, Liang Hao, Guan Zhenghui. Progress in Transition Metal-Catalyzed Reactions of Oximes and Their Derivatives [J]. Chin. J. Org. Chem., 2013, 33(01): 66-75.
[14]	Xu Qing, Zhao Changqiu, Zhou Yongbo, Yin Shuangfeng, Han Libiao. Transition Metal-Catalyzed Transformations of P(O)—H Bonds [J]. Chin. J. Org. Chem., 2012, 32(10): 1761-1775.
[15]	SONG Zi-Wei, ZHU Jing-Jing, CHEN Xin, LIU Pu. Synthesis, Characterization and Catalytic Performance of PAMAM- Salicylidene Schiff Base Dendrimer Palladium Complex [J]. Chin. J. Org. Chem., 2011, 31(11): 1835-1841.