SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 3: 1136 - 1145

DOI: https://doi.org/10.6023/cjoc202211013

ARTICLES

Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers

  • Rui Wang ,
  • Lang Gao ,
  • Cen Zhou ,
  • Xiao Zhang
Expand
  • a Fujian Key Laboratory of Polymer Materials, Fujian Provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350007
    b Fujian Engineering and Research Center of New Chinese Lacquer Materials, College of Materials and Chemical Engineering, Minjiang University, Fuzhou 350108
† These authors contributed equally to this work.
* Corresponding author. E-mail:

Received date: 2022-11-10

  Revised date: 2023-01-10

  Online published: 2023-01-18

Supported by

National Natural Science Foundation of China(22071024); National Natural Science Foundation of China(22271047); Natural Science Foundation of Fujian Province(2021J06020); Natural Science Foundation of Fujian Province(2022J011121); Science and Technology Project of Minjiang University(MJY21027)

Fold

Abstract

Photocatalytic heterogeneous chlorotrifluoromethylation and iodoperfluoroalkylation of unactivated terminal alkenes have been achieved under the catalysis of phenylphenothiazine-based porous organic polymer (PTH-POP). This method offers a transition-metal-free and recyclable platform to access valuable perfluoroalkylated compounds in a highly efficient fashion.

Key words： chlorotrifluoromethylation; heterogeneous; porous organic polymer; recyclability; transition-metal-free

Cite this article

Rui Wang , Lang Gao , Cen Zhou , Xiao Zhang . Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers[J]. Chinese Journal of Organic Chemistry, 2023 , 43(3) : 1136 -1145 . DOI: 10.6023/cjoc202211013

References

[1]
For selected reviews on visible-light photocatalysis, see: (a) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828.
[1]
(b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[1]
(c) Lang, X.; Chen, X.; Zhao, J. Chem. Soc. Rev. 2014, 43, 473.
[1]
(d) Zeng, L.; Guo, X.; He, C.; Duan, C. ACS Catal. 2016, 6, 7935.
[1]
(e) Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850.
[1]
(f) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
[1]
(g) Teixeira, I. F.; Barbosa, E. C. M.; Tsan, S. C. E.; Camargo, P. H. C. Chem. Soc. Rev. 2018, 47, 7783.
[1]
(h) Marzo, L.; Pagire, S. K.; Reiser, O.; K?nig, B. Angew. Chem., Int. Ed. 2018, 57, 10034.
[1]
(i) Chen, Y.; Lu, L.-Q.; Yu, D.-G.; Zhu, C.-J.; Xiao, W.-J. Sci. China: Chem. 2019, 62, 24.
[1]
(j) Riente, P.; No?l, T. Catal. Sci. Technol. 2019, 9, 5186.
[1]
(k) Li, J.-Y.; Li, Y.-H.; Qi, M.-Y.; Lin, Q.; Tang, Z.-R.; Xu, Y.-J. ACS Catal. 2020, 10, 6262.
[1]
(l) Wu, H.-L.; Li, X.-B.; Tung, C.-H.; Wu, L.-Z. Chem. Commun. 2020, 56, 15496.
[1]
(m) Liu, J.; Fu, W.; Liao, Y.; Fan, J.; Xiang, Q. J. Mater. Sci. Technol. 2021, 91, 224.
[1]
(n) Tlili, A.; Lakhdar, S. Angew. Chem., Int. Ed. 2021, 60, 19526.
[1]
(o) Cheng, Y.-Z.; Feng, Z.; Zhang, X.; You, S.-L. Chem. Soc. Rev. 2022, 51, 2145.
[2]
For selected reviews, see: (a) Wong, Y.-L.; Tobin, J. M.; Xu, Z.; Vilela, F. J. Mater. Chem. A 2016, 4, 18677.
[2]
(b) Li, R.; Byun, J.; Huang, W.; Ayed, C.; Wang, L.; Zhang, K. A. I. ACS Catal. 2018, 8, 4735.
[2]
(c) Byun, J.; Zhang, K. A. I. Mater. Horiz. 2020, 7, 15.
[2]
(d) Zhang, T.; Xing, G.; Chen, W.; Chen, L. Mater. Chem. Front. 2020, 4, 332.
[2]
(e) Gisbertz, S.; Pieber, B. ChemPhotoChem 2020, 4, 456.
[2]
(f) Xu, Z.-Y.; Luo, Y.; Wang, H.; Zhang, D.-W.; Li, Z.-T. Chin. J. Org. Chem. 2020, 40, 3777. (in Chinese)
[2]
(徐子悦, 罗驿, 王辉, 张丹维, 黎占亭, 有机化学, 2020, 40, 3777.)
[2]
(g) Luo, S.; Zeng, Z.; Zeng, G.; Liu, Z.; Xiao, R.; Xu, P.; Wang, H.; Huang, D.; Liu, Y.; Shao, B.; Liang, Q.; Wang, D.; He, Q.; Qin, L.; Fu, Y. J. Mater. Chem. A 2020, 8, 6434.
[2]
(h) Wang, T.-X.; Liang, H.-P.; Anito, D. A.; Ding, X.; Han, B.-H. J. Mater. Chem. A 2020, 8, 7003.
[2]
(i) Xiao, J.; Liu, X.; Pan, L.; Shi, C.; Zhang, X.; Zou, J.-J. ACS Catal. 2020, 10, 12256.
[2]
(j) Ferguson, C. T. J.; Zhang, K. A. I. ACS Catal. 2021, 11, 9547.
[2]
(k) Ji, W.; Wang, T.-X.; Ding, X.; Lei, S.; Han, B.-H. Coord. Chem. Rev. 2021, 439, 213875.
[2]
(l) Qian, Z.; Zhang, K. A. I. Sol. RRL. 2021, 5, 2000489.
[2]
(m) Zhang, Z.; Jia, J.; Zhi, Y.; Ma, S.; Liu, X. Chem. Soc. Rev. 2022, 51, 2444.
[2]
For selected examples, see:
[2]
(n) Gui, Q.-W.; Teng, F.; Li, Z.-C.; Xiong, Z.-Y.; Jin, X.-F.; Lin, T.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 1907.
[2]
(o) Wang, Z.; Liu, Q.; Liu, R.; Ji, Z.; Li, Y.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2022, 33, 1479.
[2]
(p) Ma, C.-H.; Zhao, L.; He, X.; Jiang, Y.-Q.; Yu, B. Org. Chem. Front. 2022, 9, 1445.
[3]
For selected examples, see: (a) Liang, H.-P.; Chen, Q.; Han, B.-H. ACS Catal. 2018, 8, 5313.
[3]
(b) Luo, J.; Lu, J.; Zhang, J. J. Mater. Chem. A 2018, 6, 15154.
[3]
(c) Zhi, Y.; Ma, S.; Xia, H.; Zhang, Y.; Shi, Z.; Mu, Y.; Liu, X. Appl. Catal. B 2019, 244, 36.
[3]
(d) Zhang, W.; Li, S.; Tang, X.; Tang, J.; Pan, C.; Yu, G. Appl. Catal. B 2020, 272, 118982.
[3]
(e) Xu, Z.-Y.; Luo, Y.; Zhang, D.-W.; Wang, H.; Sun, X.-W.; Li, Z.-T. Green Chem. 2020, 22, 136.
[3]
(f) An, W.-K.; Zheng, S.-J.; Zhang, H.-X.; Shang, T.-T.; Wang, H.-R.; Xu, X.-J.; Jin, Q.; Qin, Y.; Ren, Y.; Jiang, S.; Xu, C.-L.; Hou, M.-S.; Pan, Z. Green Chem. 2021, 23, 1292.
[3]
(g) Liu, H.-K.; Lei, Y.-F.; Tian, P.-J.; Wang, H.; Zhao, X.; Li, Z.-T.; Zhang, D.-W. J. Mater. Chem. A 2021, 9, 6361.
[3]
(h) Guo, L.; Wang, X.; Zhan, Z.; Zhao, Y.; Chen, L.; Liu, T.; Tan, B.; Jin, S. Chem. Mater. 2021, 33, 1994.
[3]
(i) Li, S.; Zhang, W.; Yang, S.; Chen, F.; Pan, C.; Tang, J.; Zhang, K. A. I.; Yu, G. Chem. Eng. J. 2021, 408, 127261.
[3]
(j) Zhang, H.; Zhou, C.; Zheng, Y.; Zhang, X. Green Chem. 2021, 23, 8878.
[3]
(k) Fu, X.-Y.; Si, Y.-F.; Qiao, L.-P.; Zhao, Y.-F.; Chen, X.-L.; Yu, B. Adv. Synth. Catal. 2022, 364, 574.
[3]
(l) Zhu, S.-S.; Liu, Y.; Chen, X.-L.; Qu, L.-B.; Yu, B. ACS Catal. 2022, 12, 126.
[3]
(m) Li, X.; Zhang, F.; Wang, Y.; Xiong, K.; Lang, X. J. Mater. Chem. A 2022, 10, 14965.
[3]
(n) Zhou, C.; Wang, R.; Gao, L.; Huang, X.; Zhang, X. ACS Appl. Mater. Interfaces 2022, 14, 30962.
[3]
(o) Lan, F.; Liu, C.-S.; Zhou, C.; Huang, X.; Wu, J.-Y.; Zhang, X. J. Mater. Chem. A 2022, 10, 16578.
[3]
(p) An, W.-K.; Zheng, S.-J.; Xu, X.; Liu, L.-J.; Ren, J.-S.; Fan, L.; Yang, Z.-K.; Ren, Y.; Xu, C. Appl. Catal. B 2022, 316, 121630.
[3]
(q) Zhu, S.-S.; Zuo, L.; Liu, Y.; Yu, B. Green Chem. 2022, 24, 8725.
[3]
(r) Shi, A.; Sun, K.; Wu, Y.; Xiang, P.; Krylov, I. B.; Terent’ev, A. O.; Chen, X.; Yu, B. J. Catal. 2022, 415, 28.
[3]
(s) Huang, X.; Liu, S.; Liu, G.; Tao, Y.; Wang, C.; Zhang, Y.; Li, Z.; Wang, H.; Zhou, Z.; Shen, G.; Xue, Z.; Sun, D. Appl. Catal. B 2023, 323, 122134.
[4]
(a) Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
[4]
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[4]
(c) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
[4]
(d) Wang, J.; Sánchez-Roselló, M.; Acen?a, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
[5]
For selected reviews, see: (a) Liu, H.; Gu, Z.; Jiang, X. Adv. Synth. Catal. 2013, 355, 617.
[5]
(b) Koike, T.; Akita, M. Top. Catal. 2014, 57, 967.
[5]
(c) Zhang, C. Adv. Synth. Catal. 2014, 356, 2895.
[5]
(d) Barata-Vallejo, S.; Bonesi, S. M.; Postigo, A. Org. Biomol. Chem. 2015, 13, 11153.
[5]
(e) Chatterjee, T.; Iqbal, N.; You, Y.; Cho, E. J. Acc. Chem. Res. 2016, 49, 2284.
[5]
For selected examples, see:
[5]
(f) Liu, J.; Li, L.; Yu, L.; Tang, L.; Chen, Q.; Shi, M. Adv. Synth. Catal. 2018, 360, 2959.
[5]
(g) Zhu, M.; Zhou, K.; Zhang, X.; You, S.-L. Org. Lett. 2018, 20, 4379.
[5]
(h) Wei, Z.; Qi, S.; Xu, Y.; Liu, H.; Wu, J.; Li, H.; Xia, C.; Duan, G. Adv. Synth. Catal. 2019, 361, 5490.
[5]
(i) Guo, Y.-Q.; Wang, K.; Wang, R.; Song, H.; Liu, Y.; Wang, Q. Adv. Synth. Catal. 2021, 363, 1651.
[6]
For a recent review, see: (a) Fu, B.; Escorihuela, J.; Han, J.; Fustero, S.; Barrio, P.; Sodeoka, M.; Kawamura, S.; Sorochinsky, A.; Soloshonok, V. A. Molecules 2021, 26, 7221.
[6]
For selected examples, see: (b) Oh, S. H.; Malpani, Y. R.; Ha, N.; Jung, Y.-S.; Han, S. B. Org. Lett. 2014, 16, 1310.
[6]
(c) Tang, X.-J.; Dolbier Jr, W. R. Angew. Chem., Int. Ed. 2015, 54, 4246.
[6]
(d) Bagal, D. B.; Kachkovskyi, G.; Knorn, M.; Rawner, T.; Bhanage, B. M.; Reiser, O. Angew. Chem., Int. Ed. 2015, 54, 6999.
[6]
(e) Alkan-Zambada, M.; Hu, X. Organometallics 2018, 37, 3928.
[6]
(f) Zhang, W.; Lin, J.-H.; Xiao, J.-C. J. Fluorine Chem. 2018, 215, 25.
[6]
(g) Nicholls, T. P.; Caporale, C.; Massi, M.; Gardiner, M. G.; Bissember, A. C. Dalton Trans. 2019, 48, 7290.
[6]
(h) Maeda, K.; Kurahashi, T.; Matsubara, S. Eur. J. Org. Chem. 2019, 2019, 4613.
[6]
(i) Engl, S.; Reiser, O. Eur. J. Org. Chem. 2020, 2020, 1523.
[6]
(j) Wu, D.; Fan, W.; Wu, L.; Chen, P.; Liu, G. ACS Catal. 2022, 12, 5284.
[7]
Quan, Y.; Shi, W.; Song, Y.; Jiang, X.; Wang, C.; Lin, W. J. Am. Chem. Soc. 2021, 143, 3075.
[8]
Shi, Y.; Zhang, T.; Jiang, X.-M.; Xu, G.; He, C.; Duan, C. Nat. Commun. 2020, 11, 5384.
[9]
For selected examples, see: (a) Treat, N. J.; Sprafke, H.; Kramer, J. W.; Clark, P. G.; Barton, B. E.; Alaniz, J. R. D.; Fors, B. P.; Hawker, C. J. J. Am. Chem. Soc. 2014, 136, 16096.
[9]
(b) Wang, H.; Jui, N. T. J. Am. Chem. Soc. 2018, 140, 163.
[9]
(c) Speck, F.; Rombach, D.; Wagenknecht, H.-A. Beilstein J. Org. Chem. 2019, 15, 52.
[9]
(d) Lu, F.-D.; Liu, D.; Zhu, L.; Lu, L.-Q.; Yang, Q.; Zhou, Q.-Q.; Wei, Y.; Lan, Y.; Xiao, W.-J. J. Am. Chem. Soc. 2019, 141, 6167.
[9]
(e) Wang, R.; Zhou, C.; Huang, X.; Wu, J.-Y.; Zhang, X. ACS Sustainable Chem. Eng. 2022, 10, 4650.
[10]
For selected reviews, see: (a) Bag, D.; Kour, H.; Sawant, S. D. Org. Biomol. Chem. 2020, 18, 8278.
[10]
(b) Liu, T.; Liu, J.; He, J.; Hong, Y.; Zhou, H.; Liu, Y.-L.; Tang, S. Synthesis 2022, 54, 1919.
[10]
For selected examples, see: (c) Wallentin, C.-J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875.
[10]
(d) Mao, L.-L.; Cong, H. ChemSusChem 2017, 10, 4461.
[10]
(e) Rawner, T.; Lutsker, E.; Kaiser, C. A.; Reiser, O. ACS Catal. 2018, 8, 3950.
[10]
(f) Zhang, T.; Wang, P.; Gao, Z.; An, Y.; He, C.; Duan, C. RSC Adv. 2018, 8, 32610.
[10]
(g) Filippini, G.; Longobardo, F.; Forster, L.; Criado, A.; Di Carmine, G.; Nasi, L.; D’Agostino, C.; Melchionna, M.; Fornasiero, P.; Prato, M. Sci. Adv. 2020, 6, eabc9923.
[10]
(h) Liu, Z.; Li, C.; Chen, J.; Li, X.; Luo, F.; Cheng, F.; Liu, J.-J. Inorg. Chem. Front. 2022, 9, 111.
[11]
Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224.
[12]
Cismesia, M. A.; Yoon, T. P. Chem. Sci. 2015, 6, 5426.
[13]
Li, Z.; Wang, J.-A.; Ma, S.; Zhang, Z.; Zhi, Y.; Zhang, F.; Xia, H.; Henkelman, G.; Liu, X. Appl. Catal. B 2022, 310, 121335.
[14]
Beniazza, R.; Atkinson, R.; Absalon, C.; Castet, F.; Denisov, S. A.; McClenaghan, N. D.; Laste?coue?res, D.; Vincent, J. M. Adv. Synth. Catal. 2016, 358, 2949.
Options
Outlines

/

〈 〉