ARTICLES

Visible Light Induced Arylfluoroalkylation of Activated Alkenes

  • Xinling Li ,
  • Weidong Meng ,
  • Xiuhua Xu ,
  • Yan'gen Huang
Expand
  • a Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620
    b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2022-01-10

  Revised date: 2022-01-29

  Online published: 2022-02-18

Supported by

National Natural Science Foundation of China(2199121)

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.

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 . DOI: 10.6023/cjoc202201011

References

[1]
(a) Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815. (in Chinese)
[1]
( 卿凤翎, 有机化学, 2012, 32, 815.)
[1]
(b) Gouverneur, V.; Seppelt, K. Chem. Rev. 2015, 115, 563.
[1]
(c) Champagne, P. A.; Desroches, J.; Hamel, J. D.; Vandamme, M.; Paquin, J.-F. Chem. Rev. 2015, 115, 9073.
[1]
(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)
[1]
( 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.)
[2]
(a) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
[2]
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[2]
(c) Gou, B. Q.; Yang, C.; Zhang, L.; Xia, W. J. Acta. Chim. Sin. 2017, 75, 66. (in Chinese)
[2]
( 苟宝权, 杨超, 张磊, 夏吾炯, 化学学报, 2017, 75, 66.)
[3]
Obermeier, M. R.; Kapusta, G. Weed Technol. 1996, 10, 689.
[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.
[5]
(a) Chen, D.; Yang, W.; Yao, Y.; Yang, X.; Deng, Y.; Yang, D. Chin. J. Org.Chem. 2018, 38, 2571. (in Chinese)
[5]
( 陈董涵, 杨文, 姚永祺, 有机化学, 2018, 38, 2571.)
[5]
(b) Vaishak, T. B.; Soumya, P. K.; Saranya, P. V.; Anilkumar, G. Catal. Sci. Technol. 2021, 11, 4690.
[5]
(c) Bhaskaran, R. P.; Babu, B. P. Adv. Synth. Catal. 2020, 362, 5219.
[5]
(d) Hu, W.-Q.; Pan, S.; Xu, X.-H.; Vicic, D. A.; Qing, F.-L. Angew. Chem., Int. Ed. 2020, 59, 16076.
[5]
(e) Xiao, H.; Zhang, Z.; Fang, Y.; Zhu, L.; Li, C. Chem. Soc. Rev. 2021, 50, 6308.
[5]
(f) Gietter-Burch, A. A. S.; Devannah, V.; Watson, D. A. Org. Lett. 2017, 19, 2957.
[5]
(g) Li, B.; Zeng, W.; Wang, L.; Geng, Z.; Loh, T.-P.; Xie, P. Org. Lett. 2021, 23, 5235.
[5]
(h) Li, W.; Zhou, X.; Xiao, T.; Ke, Z.; Zhou, L. CCS Chem. 2021, 3, 794.
[5]
(i) Liang, S.; Wei, J.; Jiang, L.; Liu, J.; Mumtaz, Y.; Yi, W. CCS Chem. 2021, 3, 265.
[6]
(a) Fu, W.; Zhu, M.; Zou, G.; Xu, C.; Wang, Z. Synlett 2014, 25, 2513.
[6]
(b) Hwang, J.; Park, K.; Choe, J.; Min, H.; Song, K. H.; Lee, S. J. Org. Chem. 2014, 79, 3267.
[6]
(c) Zhang, Y.; Du, H.; Zhu, M.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Tetrahedron Lett. 2017, 58, 880.
[6]
(d) Fang, J.; Fan, W.; Feng, B. Chin. J. Org.Chem. 2018, 38, 2666. (in Chinese)
[6]
( 方洁梅, 范为正, 冯柏年, 有机化学, 2018, 38, 2666.)
[7]
(a) Fuji, K. Chem. Rev. 1993, 93, 2037.
[7]
(b) Biswas, P.; Guin, J. J. Org.Chem. 2018, 83, 5629.
[7]
(c) Caporaso, R.; Manna, S.; Zinken, S.; Kochnev, A. R.; Lukyanenko, E. R.; Kurkin, A. V.; Antonchick, A. P. Chem. Commun. 2016, 52, 12486.
[7]
(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.
[7]
(e) Shi, L. L.; Wang, H.; Yang, H. J.; Fu, H. Synlett 2015, 26, 688.
[8]
(a) Kong, W.; Casimiro, M.; Merino, E.; Nevado, C. J. Am. Chem. Soc. 2013, 135, 14480.
[8]
(b) Kong, W.; Casimiro, M.; Fuentes, N.; Meri-no, E.; Nevado, C. Angew. Chem., Int. Ed. 2013, 52, 13086.
[9]
Niu, B.; Xie, P.; Zhao, W.; Zhou, Y.; Bian, Z.; Pittman, C. U.; Zhou, A. RSC Adv. 2014, 4, 43525.
[10]
Tian, Q.; He, P.; Kuang, C. Org. Biomol. Chem. 2014, 12, 6349.
[11]
Zhang, M.; Sheng, W.; Ji, P.; Liu, Y.; Guo, C. RSC Adv. 2015, 5, 56438.
[12]
Xia, X. F.; Zhu, S. L.; Chen, C.; Wang, H.; Liang, Y. M. J. Org. Chem. 2016, 81, 1277.
[13]
Zhang, H. L.; Pan, C. D.; Jin, N.; Gu, Z. X.; Hu, H. W.; Zhu, C. J. Chem. Commun. 2015, 51, 1320.
[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.
[15]
Yu, J. T.; Chen, R.; Zhu, J.; Cheng, J. Org. Biomol. Chem. 2017, 15, 5476.
[16]
Yu, J. T.; Hu, W. M.; Peng, H. B.; Cheng, J. Tetrahedron Lett. 2016, 57, 4109.
[17]
Ni, Z. Q.; Huang, X.; Pan, Y. J. Org. Lett. 2016, 18, 2612.
[18]
Qiu, J. K.; Hao, W. J.; Kong, L. F.; Ping, W.; Tu, S. J.; Jiang, B. Tetrahedron Lett. 2016, 57, 2414.
[19]
Liu, C.; Zhang, B. RSC Adv. 2015, 5, 61199.
[20]
He, Z. B.; Tan, P.; Ni, C. F.; Hu, J. B. Org. Lett. 2015, 17, 1838.
[21]
Fa, J. H.; Yang, J.; Song, R. J.; Li, J. H. Org. Lett. 2015, 17, 836.
[22]
Liu, K.; Sui, L. C.; Jin, Q.; Li, D. Y.; Liu, P. N. Org. Chem. Front. 2017, 4, 1606.
[23]
(a) Zheng, J.; Chen, Q. Y.; Sun, K.; Huang, Y. G.; Guo, Y. Tetrahedron Lett. 2016, 57, 5757.
[23]
(b) Han, E. J.; Sun, Y.; Shen, Q.; Chen, Q. Y.; Guo, Y.; Huang, Y. G. Org. Chem. Front. 2015, 2, 1379.
[23]
(c) Yang, X.; Meng, W. D.; Xu, X. H.; Huang, Y. Org. Chem. Front. 2021, 8, 6597.
[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.
[25]
(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.
[25]
(c) He, B.; Pan, Q. J.; Guo, Y.; Chen, Q. Y.; Liu, C. Org. Lett. 2020, 22, 6552.
[26]
Biswas, P.; Guin, J. J. Org. Chem. 2018, 83, 5629.
[27]
(a) Zheng, L. W.; Yang, C.; Xu, Z. Z.; Gao, F.; Xia, W. J. J. Org. Chem. 2015, 80, 5730.
[27]
(b) Yu, W.; Xu, X.-H.; Qing, F.-L. Org. Lett. 2016, 18, 5130.
[27]
(c) Wang, P.; Zhao, Q.; Xiao, W.; Chen, J. Green Synth. Catal. 2020, 1, 42.
Outlines

/

〈 〉