Visible Light Induced Arylfluoroalkylation of Activated Alkenes

doi:10.6023/cjoc202201011

Abstract

Fluorine-containing compounds have a wide range of applications in the fields of biomedicine and materials, and the development of synthetic methodology for fluorine-containing compounds is very important. Using fac-Ir(ppy)₃ as catalyst, a wide variety of amides containing fluoroalkyl substituted α-quaternary carbon center were prepared with N-aryl-N-(aryl- sulfonyl)-2-methyl acrylamides as starting materials by visible light induced cascade fluoroalkyl radical addition, aryl migration and desulfonylation. The reaction conditions are mild, and possess good functional group compatibility.

Key words: photocatalysis, fluoroalkylation, aryl migration, desulfonylation, α-quaternary carbon center, amide

Cite this article

Xinling Li, Weidong Meng, Xiuhua Xu, Yan'gen Huang. Visible Light Induced Arylfluoroalkylation of Activated Alkenes[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1820-1830.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

References 27

[1]	(a) Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815. (in Chinese) pmid: 25627818
	( 卿凤翎, 有机化学, 2012, 32, 815.) doi: 10.6023/cjoc1202021 pmid: 25627818
	(b) Gouverneur, V.; Seppelt, K. Chem. Rev. 2015, 115, 563. doi: 10.1021/cr500686k pmid: 25627818
	(c) Champagne, P. A.; Desroches, J.; Hamel, J. D.; Vandamme, M.; Paquin, J.-F. Chem. Rev. 2015, 115, 9073. pmid: 25627818
	(d) Yang, J. Y.; Huang, D. F.; Wang, K. H.; Wang, J. J.; Su, Y. P.; Deng, Z. B.; Yang, T. Y.; Hu, Y. L. Chin. J. Org. Chem. 2021, 41, 2019. (in Chinese) pmid: 25627818
	( 杨金宇, 黄丹凤, 王克虎, 王君姣, 苏瀛鹏, 邓周斌, 杨天宇, 胡雨来, 有机化学, 2021, 41, 2019.) pmid: 25627818
[2]	(a) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315. doi: 10.1021/acs.jmedchem.5b00258 pmid: 26200936
	(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. doi: 10.1039/B610213C pmid: 26200936
	(c) Gou, B. Q.; Yang, C.; Zhang, L.; Xia, W. J. Acta. Chim. Sin. 2017, 75, 66. (in Chinese) pmid: 26200936
	( 苟宝权, 杨超, 张磊, 夏吾炯, 化学学报, 2017, 75, 66.) doi: 10.6023/A16070341 pmid: 26200936
[3]	Obermeier, M. R.; Kapusta, G. Weed Technol. 1996, 10, 689. doi: 10.1017/S0890037X00040665
[4]	Nauen, R.; Jeschke, P.; Velten, R.; Beck, M. E.; Ebbinghaus-Kintscher, U.; Thielert, W.; Wolfel, K.; Haas, M.; Kunz, K.; Raupach, G. Pest Manage. Sci. 2015, 71, 850. doi: 10.1002/ps.3932
[5]	(a) Chen, D.; Yang, W.; Yao, Y.; Yang, X.; Deng, Y.; Yang, D. Chin. J. Org.Chem. 2018, 38, 2571. (in Chinese) pmid: 28535057
	( 陈董涵, 杨文, 姚永祺, 有机化学, 2018, 38, 2571.) doi: 10.6023/cjoc201803045 pmid: 28535057
	(b) Vaishak, T. B.; Soumya, P. K.; Saranya, P. V.; Anilkumar, G. Catal. Sci. Technol. 2021, 11, 4690. doi: 10.1039/D1CY00499A pmid: 28535057
	(c) Bhaskaran, R. P.; Babu, B. P. Adv. Synth. Catal. 2020, 362, 5219. doi: 10.1002/adsc.202000996 pmid: 28535057
	(d) Hu, W.-Q.; Pan, S.; Xu, X.-H.; Vicic, D. A.; Qing, F.-L. Angew. Chem., Int. Ed. 2020, 59, 16076. doi: 10.1002/anie.202004116 pmid: 28535057
	(e) Xiao, H.; Zhang, Z.; Fang, Y.; Zhu, L.; Li, C. Chem. Soc. Rev. 2021, 50, 6308. pmid: 28535057
	(f) Gietter-Burch, A. A. S.; Devannah, V.; Watson, D. A. Org. Lett. 2017, 19, 2957. doi: 10.1021/acs.orglett.7b01196 pmid: 28535057
	(g) Li, B.; Zeng, W.; Wang, L.; Geng, Z.; Loh, T.-P.; Xie, P. Org. Lett. 2021, 23, 5235. doi: 10.1021/acs.orglett.1c01767 pmid: 28535057
	(h) Li, W.; Zhou, X.; Xiao, T.; Ke, Z.; Zhou, L. CCS Chem. 2021, 3, 794. pmid: 28535057
	(i) Liang, S.; Wei, J.; Jiang, L.; Liu, J.; Mumtaz, Y.; Yi, W. CCS Chem. 2021, 3, 265. doi: 10.31635/ccschem.020.202000577 pmid: 28535057
[6]	(a) Fu, W.; Zhu, M.; Zou, G.; Xu, C.; Wang, Z. Synlett 2014, 25, 2513. doi: 10.1055/s-0034-1379071
	(b) Hwang, J.; Park, K.; Choe, J.; Min, H.; Song, K. H.; Lee, S. J. Org. Chem. 2014, 79, 3267. doi: 10.1021/jo5003032
	(c) Zhang, Y.; Du, H.; Zhu, M.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Tetrahedron Lett. 2017, 58, 880. doi: 10.1016/j.tetlet.2017.01.060
	(d) Fang, J.; Fan, W.; Feng, B. Chin. J. Org.Chem. 2018, 38, 2666. (in Chinese)
	( 方洁梅, 范为正, 冯柏年, 有机化学, 2018, 38, 2666.) doi: 10.6023/cjoc201804030
[7]	(a) Fuji, K. Chem. Rev. 1993, 93, 2037. doi: 10.1021/cr00022a005
	(b) Biswas, P.; Guin, J. J. Org.Chem. 2018, 83, 5629.
	(c) Caporaso, R.; Manna, S.; Zinken, S.; Kochnev, A. R.; Lukyanenko, E. R.; Kurkin, A. V.; Antonchick, A. P. Chem. Commun. 2016, 52, 12486. doi: 10.1039/C6CC07196A
	(d) Niu, B.; Xie, P.; Bian, Z. G.; Zhao, W. N.; Zhang, M.; Zhou, Y.; Feng, L.; Pittman, C. U.; Zhou, A. H. Synlett 2015, 26, 635.
	(e) Shi, L. L.; Wang, H.; Yang, H. J.; Fu, H. Synlett 2015, 26, 688. doi: 10.1055/s-0034-1379940
[8]	(a) Kong, W.; Casimiro, M.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2013, 135, 14480. doi: 10.1021/ja403954g
	(b) Kong, W.; Casimiro, M.; Fuentes, N.; Meri-no, E.; Nevado, C. Angew. Chem., Int. Ed. 2013, 52, 13086. doi: 10.1002/anie.201307377
[9]	Niu, B.; Xie, P.; Zhao, W.; Zhou, Y.; Bian, Z.; Pittman, C. U.; Zhou, A. RSC Adv. 2014, 4, 43525. doi: 10.1039/C4RA06810F
[10]	Tian, Q.; He, P.; Kuang, C. Org. Biomol. Chem. 2014, 12, 6349. doi: 10.1039/C4OB01231C
[11]	Zhang, M.; Sheng, W.; Ji, P.; Liu, Y.; Guo, C. RSC Adv. 2015, 5, 56438. doi: 10.1039/C5RA10084D
[12]	Xia, X. F.; Zhu, S. L.; Chen, C.; Wang, H.; Liang, Y. M. J. Org. Chem. 2016, 81, 1277. doi: 10.1021/acs.joc.5b02594
[13]	Zhang, H. L.; Pan, C. D.; Jin, N.; Gu, Z. X.; Hu, H. W.; Zhu, C. J. Chem. Commun. 2015, 51, 1320. doi: 10.1039/C4CC08629E
[14]	Li, M.; Wang, C. T.; Bao, Q. F.; Qiu, Y. F.; Wei, W. X.; Li, X. S.; Wang, Y. Z.; Zhang, Z.; Wang, J. L.; Liang, Y. M. Org. Lett. 2021, 23, 751. doi: 10.1021/acs.orglett.0c03973
[15]	Yu, J. T.; Chen, R.; Zhu, J.; Cheng, J. Org. Biomol. Chem. 2017, 15, 5476. doi: 10.1039/C7OB01260H
[16]	Yu, J. T.; Hu, W. M.; Peng, H. B.; Cheng, J. Tetrahedron Lett. 2016, 57, 4109. doi: 10.1016/j.tetlet.2016.07.105
[17]	Ni, Z. Q.; Huang, X.; Pan, Y. J. Org. Lett. 2016, 18, 2612. doi: 10.1021/acs.orglett.6b01041
[18]	Qiu, J. K.; Hao, W. J.; Kong, L. F.; Ping, W.; Tu, S. J.; Jiang, B. Tetrahedron Lett. 2016, 57, 2414. doi: 10.1016/j.tetlet.2016.04.073
[19]	Liu, C.; Zhang, B. RSC Adv. 2015, 5, 61199. doi: 10.1039/C5RA08996D
[20]	He, Z. B.; Tan, P.; Ni, C. F.; Hu, J. B. Org. Lett. 2015, 17, 1838. doi: 10.1021/acs.orglett.5b00308
[21]	Fa, J. H.; Yang, J.; Song, R. J.; Li, J. H. Org. Lett. 2015, 17, 836. doi: 10.1021/ol503660a
[22]	Liu, K.; Sui, L. C.; Jin, Q.; Li, D. Y.; Liu, P. N. Org. Chem. Front. 2017, 4, 1606. doi: 10.1039/C7QO00209B
[23]	(a) Zheng, J.; Chen, Q. Y.; Sun, K.; Huang, Y. G.; Guo, Y. Tetrahedron Lett. 2016, 57, 5757.
	(b) Han, E. J.; Sun, Y.; Shen, Q.; Chen, Q. Y.; Guo, Y.; Huang, Y. G. Org. Chem. Front. 2015, 2, 1379. doi: 10.1039/C5QO00210A
	(c) Yang, X.; Meng, W. D.; Xu, X. H.; Huang, Y. Org. Chem. Front. 2021, 8, 6597. doi: 10.1039/D1QO01170G
[24]	The crystal structure has been deposited at the Cambridge Crystallographic Data Center and allocated the deposition number CCDC 2121978.
[25]	(a) Zhu, Y.; Gong, J. W.; Wang, Y. H. J. Org. Chem. 2017, 82, 7428.
	(b) Yi, N. N.; Zhang, H.; Xu, C. H.; Deng, W.; Wang, R. J.; Peng, D. M.; Zeng, Z. B.; Xiang, J. N. Org. Lett. 2016, 18, 1780. doi: 10.1021/acs.orglett.6b00498
	(c) He, B.; Pan, Q. J.; Guo, Y.; Chen, Q. Y.; Liu, C. Org. Lett. 2020, 22, 6552. doi: 10.1021/acs.orglett.0c02300
[26]	Biswas, P.; Guin, J. J. Org. Chem. 2018, 83, 5629. doi: 10.1021/acs.joc.8b00618
[27]	(a) Zheng, L. W.; Yang, C.; Xu, Z. Z.; Gao, F.; Xia, W. J. J. Org. Chem. 2015, 80, 5730.
	(b) Yu, W.; Xu, X.-H.; Qing, F.-L. Org. Lett. 2016, 18, 5130. doi: 10.1021/acs.orglett.6b02580
	(c) Wang, P.; Zhao, Q.; Xiao, W.; Chen, J. Green Synth. Catal. 2020, 1, 42.

可见光诱导活化烯烃的芳基氟烷基化反应