Progress in the Synthesis of Arylphosphonates via Ar-P Bond Construction
- Corresponding author: Luo Haiqing, luohaiq@sina.com
	            Citation:
	            
		            Sun Kai, Liu Haidong, Xie Qi, Luo Haiqing. Progress in the Synthesis of Arylphosphonates via Ar-P Bond Construction[J]. Chinese Journal of Organic Chemistry,
							;2020, 40(8): 2275-2289.
						
							doi:
								10.6023/cjoc202002006
						
					
				
					 
				
	        
 
	                
				Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681.
												 doi: 10.1021/cr040179m
											
										
				White, A. K.; Metcalf, W. W. Annu. Rev. Microbiol. 2007, 61, 379.
												 doi: 10.1146/annurev.micro.61.080706.093357
											
										
				Clercq, E. D. Med. Res. Rev. 2009, 30, 667.
												 doi: 10.1002/med.20153
											
										
Iaroshenko, V. In Organophosphorus Chemistry: From Molecules to Applications, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2019, p. 59.
				Schwan, A. L. Chem. Soc. Rev. 2004, 33, 218.
												 doi: 10.1039/B307538A
											
										
				Van der Jeught, S.; Stevens, C. V. Chem. Rev. 2009, 109, 2672.
												 doi: 10.1021/cr800315j
											
										
				Henyecz, R.; Keglevich, G. Curr. Org. Synth. 2019, 16, 523.
												 doi: 10.2174/1570179416666190415110834
											
										
				Cai, B.-G.; Xuan, J.; Xiao, W.-J. Sci. Bull. 2019, 64, 337.
												 doi: 10.1016/j.scib.2019.02.002
											
										
				Chen, T.; Zhang, J.-S.; Han, L.-B. Dalton Trans. 2016, 45, 1843.
												 doi: 10.1039/C5DT01896J
											
										
				(a) Budnikova, Y. H.; Gryaznova, T. V.; Grinenko, V. V.; Dudkina, Y. B.; Khrizanforov, M. N. Pure Appl. Chem. 2017, 89, 311. 
(b) Budnikova, Y. H.; Sinyashin, O. G. Russ. Chem. Rev. 2015, 84, 917.
				(a) Jiménez, M. V.; Pérez-Torrente, J. J.; Bartolomé, M. I.; Oro, L. A. Synthesis 2009, 1916. 
(b) Yang, Y.; Qiu, X.; Zhao, Y.; Mu, Y.; Shi, Z. J. Am. Chem. Soc. 2016, 138, 495.
				Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Synthesis 1981, 56.
										
				Hirao, T.; Masunaga, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. Bull. Chem. Soc. Jpn. 1982, 55, 909.
												 doi: 10.1246/bcsj.55.909
											
										
				Kalek, M.; Jezowska, M.; Stawinski, J. Adv. Synth. Catal. 2009, 351, 3207.
												 doi: 10.1002/adsc.200900590
											
										
				Kohler, M. C.; Sokol, J. G.; Stockland Jr, R. A. Tetrahedron Lett. 2009, 50, 457.
												 doi: 10.1016/j.tetlet.2008.11.040
											
										
				Xu, J.; Zhang, P.; Gao, Y.; Chen, Y.; Tang, G.; Zhao, Y. J. Org. Chem. 2013, 78, 8176.
												 doi: 10.1021/jo4012199
											
										
				Huang, C.; Tang, X.; Fu, H. Jiang, Y.; Zhao, Y. J. Org. Chem. 2006, 71, 5020.
												 doi: 10.1021/jo060492j
											
										
				Ballester, J.; Gatignol, J.; Schmidt, G.; Alayrac, C.; Gaumont, A.-C.; Taillefer, M. ChemCatChem 2014, 6, 1549.
												 doi: 10.1002/cctc.201301029
											
										
				Zhao, Y. L.; Wu, G. J.; Li, Y.; Gao, L. X.; Han, F. S. Chem.-Eur. J. 2012, 18, 9622.
												 doi: 10.1002/chem.201103723
											
										
				Kinbara, A.; Ito, M.; Abe, T.; Yamagishi, T. Tetrahedron 2015, 71, 7614.
												 doi: 10.1016/j.tet.2015.07.073
											
										
				Kalek, M.; Ziadi, A.; Stawinski, J. Org. Lett. 2008, 10, 4637.
												 doi: 10.1021/ol801935r
											
										
				Jablonkai, E.; Keglevich, G. Tetrahedron Lett. 2014, 44, 4185.
												 doi: 10.1002/chin.201346184
											
										
				Shaikh, R. S.; Düsel, S. J. S.; König, B. ACS Catal. 2016, 6, 8410.
												 doi: 10.1021/acscatal.6b02591
											
										
				Ghosh, I.; Shaikh, R. S.; König, B. Angew. Chem., Int. Ed. 2017, 129, 8664.
												 doi: 10.1002/ange.201703004
											
										
				Lecroq, W.; Bazille, P.; Morlet-Savary, F.; Breugst, M.; Lalevée, J.; Gaumont, A.-C.; Lakhdar, S. Org. Lett. 2018, 20, 4164.
												 doi: 10.1021/acs.orglett.8b01379
											
										
				Zeng, H.; Dou, Q.; Li, C.-J. Org. Lett. 2019, 21, 1301.
												 doi: 10.1021/acs.orglett.8b04081
											
										
				Sengmany, S.; Ollivier, A.; Le Gall, E.; Léonel, E. Org. Biomol. Chem. 2018, 16, 4495.
												 doi: 10.1039/C8OB00500A
											
										
				Wang, S.; Yang, C.; Sun, S.; Wang, J. Chem. Commun. 2019, 55, 14035.
												 doi: 10.1039/C9CC07069A
											
										
				Bai, Y.; Liu, N.; Wang, S.; Wang, S.; Ning, S.; Shi, L.; Cui, L.; Zhang, Z.; Xiang, J. Org. Lett. 2019, 21, 6835.
												 doi: 10.1021/acs.orglett.9b02475
											
										
				Andaloussi, M.; Lindh, J.; Savmarker, J.; Sjoberg, P. J. R.; Larhed, M. Chem.-Eur. J. 2009, 15, 13069.
												 doi: 10.1002/chem.200901473
											
										
				Zhuang, R.; Xu, J.; Cai, Z.; Tang, G.; Fang, M.; Zhao, Y. Org. Lett. 2011, 13, 2110.
												 doi: 10.1021/ol200465z
											
										
				Hu, G.; Chen, W.; Fu, T.; Peng, Z.; Qiao, H.; Gao, Y.; Zhao, Y. Org. Lett. 2013, 15, 5362.
												 doi: 10.1021/ol402672e
											
										
				Hicks, I.; McTague, J.; Hapatsha, T.; Teriak, R.; Kaur, P. Molecules 2020, 25, 290.
												 doi: 10.3390/molecules25020290
											
										
				Chen, T.-H.; Reddy, D. M.; Lee, C.-F. RSC Adv. 2017, 7, 30214.
												 doi: 10.1039/C7RA04619G
											
										
				Berrino, R.; Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Stabile, P. Org. Biomol. Chem. 2010, 8, 4518.
												 doi: 10.1039/c0ob00243g
											
										
				He, Y.; Wu, H.; Toste, F. D. Chem. Sci. 2015, 46, 1194.
												 doi: 10.1039/c4sc03092c
											
										
				Wang, S.; Qiu, D.; Mo, F.; Zhang, Y.; Wang, J. J. Org. Chem. 2016, 81, 11603.
												 doi: 10.1021/acs.joc.6b01820
											
										
				Xu, W.; Hu, G.; Xu, P.; Gao, Y.; Yin, Y.; Zhao, Y. Adv. Synth. Catal. 2014, 14, 2948.
												 doi: 10.1002/adsc.201400436
											
										
				Chen, S.-Y.; Zeng, R.-S.; Zou, J.-P.; Asekun, O. T. J. Org. Chem. 2014, 79, 1449.
												 doi: 10.1021/jo4022474
											
										
				Li, R.; Chen, X.; Wei, S.; Sun, K.; Fan, L.-L.; Liu, Y.; Qu, L.; Zhao, Y.; Yu, B. Adv. Synth. Catal. 2018, 360, 4807.
												 doi: 10.1002/adsc.201801122
											
										
				Qiu, D.; Lian, C.; Mao, J.; Ding, Y.; Liu, Z.; Wei, L.; Fagnoni, M.; Protti, S. Adv. Synth. Catal. 2019, 361, 5239.
												 doi: 10.1002/adsc.201900953
											
										
				Jian, Y.; Chen, M.; Huang, B.; Jia, W.; Yang, C.; Xia, W. Org. Lett. 2018, 20, 5370.
												 doi: 10.1021/acs.orglett.8b02288
											
										
				Yang, G.; Shen, C.; Zhang, L.; Zhang, W. Tetrahedron Lett. 2011, 52, 5032.
												 doi: 10.1016/j.tetlet.2011.07.077
											
										
				Yang, J.; Chen, T.; Han, L.-B. J. Am. Chem. Soc. 2015, 137, 1782.
												 doi: 10.1021/ja512498u
											
										
				Yang, J.; Xiao, J.; Chen, T.; Han, L.-B. J. Org. Chem. 2016, 81, 3911.
												 doi: 10.1021/acs.joc.6b00289
											
										
				Liao, L.-L.; Gui, Y.-Y.; Zhang, X.-B.; Shen, G.; Liu, H.-D.; Zhou, W.-J.; Li, J.; Yu, D.-G. Org. Lett. 2017, 19, 3735.
												 doi: 10.1021/acs.orglett.7b01561
											
										
				Miao, T.; Wang, L. Adv. Synth. Catal. 2014, 356, 967.
												 doi: 10.1002/adsc.201300983
											
										
				Li, J.; Bi, X.; Wang, H.; Xiao, J. RSC Adv. 2014, 4, 19214.
												 doi: 10.1039/C4RA01270D
											
										
				Yang, J.; Xiao, J.; Chen, T.; Yin, S.-F.; Han, L.-B. Chem. Commun. 2016, 52, 12233.
												 doi: 10.1039/C6CC06048J
											
										
				Feng, C. G.; Ye, M.; Xiao, K.-J.; Li, S.; Yu, J.-Q. J. Am. Chem. Soc. 2013, 135, 9322.
												 doi: 10.1021/ja404526x
											
										
				Li, C.; Yano, T.; Ishida N.; Murakami, M. Angew. Chem., Int. Ed. 2013, 52, 9801.
												 doi: 10.1002/anie.201305202
											
										
				Min, M.; Kang, D.; Jung, S.; Hong, S. Adv. Synth. Catal. 2016, 358, 1296.
												 doi: 10.1002/adsc.201600014
											
										
				Hong, G.; Mao, D.; Wu, S.; Wang, L. J. Org. Chem. 2014, 79, 10629.
												 doi: 10.1021/jo501928x
											
										
				Wang, S.; Guo, R.; Wang, G.; Chen, S.-Y.; Yu, X.-Q. Chem. Commun. 2014, 50, 12718.
												 doi: 10.1039/C4CC06246A
											
										
				Hore, S.; Srivastava, A.; Singh, R. P. J. Org. Chem. 2019, 84, 6868.
												 doi: 10.1021/acs.joc.9b00670
											
										
				Effenberger, F.; Kottmann, H. Tetrahedron 1985, 41, 4171.
												 doi: 10.1016/S0040-4020(01)97192-3
											
										
				Mao, X.; Ma, X.; Zhang, S.; Hu, H.; Zhu, C.; Cheng, Y. Eur. J. Org. Chem. 2013, 20, 4245.
										
				Kagayama, T.; Nakano, A.; Sakaguchi, S.; Ishii, Y. Org. Lett. 2006, 8, 407.
												 doi: 10.1021/ol052406s
											
										
				Berger, O.; Montchamp, J.-L. J. Org. Chem. 2019, 84, 9239.
												 doi: 10.1021/acs.joc.9b01239
											
										
				Niu, L.; Liu, J.; Yi, H. Wang, S.; Liang, X.-A.; Singh, A. K.; Chiang, C.-W.; Lei, A. ACS Catal. 2017, 7, 7412.
												 doi: 10.1021/acscatal.7b02418
											
										
				Yuan, Y.; Qiao, J.; Cao, Y.; Tang, J.; Wang, M.; Ke, G.; Lu, Y.; Liu, X.; Lei, A. Chem. Commun. 2019, 55, 4230.
												 doi: 10.1039/C9CC00975B
											
										
				Liu, C.; Szostak, M. Angew. Chem., Int. Ed. 2017, 56, 12718.
												 doi: 10.1002/anie.201707102
											
										
				Isshiki, R.; Muto, K.; Yamaguchi, J. Org. Lett. 2018, 20, 1150.
												 doi: 10.1021/acs.orglett.8b00080
											
										
				Dong, J.; Liu, L.; Ji, X.; Shang, Q.; Liu, L.; Su, L.; Chen, B.; Kan, R.; Zhou, Y.; Yin, S.-F.; Han, L.-B. Org. Lett. 2019, 21, 3198.
												 doi: 10.1021/acs.orglett.9b00922
											
										
				Li, J.; Bi, X.; Wang, H.; Xiao, J. Asian J. Org. Chem. 2014, 3, 1113.
												 doi: 10.1002/ajoc.201402088
											
										
				Liu, C.; Ji, C.-L.; Zhou, T.; Hong, X.; Szostak, M. Org. Lett. 2019, 21, 9256.
												 doi: 10.1021/acs.orglett.9b03678
											
										
				Dhokale, R. A.; Mhaske, S. B. Org. Lett. 2013, 15, 2218.
												 doi: 10.1021/ol400780f
											
										
				Chen, Q.; Yan, X.; Du, Z.; Zhang, K.; Wen, C. J. Org. Chem. 2016, 81, 276.
												 doi: 10.1021/acs.joc.5b02308
											
										
				Yang, G.; Shen, C.; Quan, M.; Zhang, W. Tetrahedron 2016, 72, 333.
												 doi: 10.1016/j.tet.2015.11.045
											
										
				Wang, T.; Sang, S.; Liu, L.; Qiao, H.; Gao, Y.; Zhao, Y. J. Org. Chem. 2014, 79, 608.
												 doi: 10.1021/jo402392t
											
										
				Luo, H.; Liu, H.; Chen, X.; Wang, K.; Luo, X.; Wang, K. Chem. Commun. 2017, 53, 956.
												 doi: 10.1039/C6CC08408G
											
										
				Matsumura, M.; Dong, Y.; Kakusawa, N.; Yasuike, S. Chem. Pharm. Bull. 2015, 63, 130.
												 doi: 10.1248/cpb.c14-00727
											
										
				Yu, Y.; Yi, S.; Zhu, C.; Hu, W.; Gao, B.; Chen, Y.; Wu, W.; Jiang, H. Org. Lett. 2016, 18, 400.
												 doi: 10.1021/acs.orglett.5b03415
											
										
 
						
						
						
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