Citation: Wang Na, Gu Qiang-Shuai, Cheng Yong-Feng, Li Lei, Li Zhong-Liang, Guo Zhen, Liu Xin-Yuan. Visible-Light Promoted Preparation of Trifluoromethylated Tetrahydrofuran and Tetrahydropyran[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 200-206. doi: 10.6023/cjoc201808048 shu

Visible-Light Promoted Preparation of Trifluoromethylated Tetrahydrofuran and Tetrahydropyran

Wang Na ^a,b ,
Gu Qiang-Shuai ^c,, ,
Cheng Yong-Feng ^a ,
Li Lei ^a ,
Li Zhong-Liang ^c ,
Guo Zhen ^b,, ,
Liu Xin-Yuan ^a,,

a.
Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055
b.
Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education, College of Materials Science & Engineering, Taiyuan University of Technology, Shanxi 030024
c.
SUSTech Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen 518055

Corresponding author: Gu Qiang-Shuai, guqs@sustc.edu.cn Guo Zhen, guozhen@tyut.edu.cn Liu Xin-Yuan, liuxy3@sustc.edu.cn
Received Date: 31 August 2018
Revised Date: 26 September 2018
Available Online: 19 January 2018
Fund Project: the National Natural Science Foundation of China 21831002the Shenzhen Nobel Prize Scientists Laboratory Project C17213101Project supported by the National Natural Science Foundation of China (Nos. 21722203, 21831002, 21801116, and 21572096), the Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy, and New Material Industries (Nos. JCYJ20170412152435366, JCYJ20170307105638498), the Natural Science Foundation of Guangdong Province (No. 2018A030310083) and the Shenzhen Nobel Prize Scientists Laboratory Project (No. C17213101)the Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy, and New Material Industries JCYJ20170412152435366the National Natural Science Foundation of China 21801116the Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy, and New Material Industries JCYJ-20170307105638498the National Natural Science Foundation of China 21722203the Natural Science Foundation of Guangdong Province 2018A030310083the National Natural Science Foundation of China 21572096

Figures(2)

An efficient protocol for facile access to trifluoromethylated tetrahydrofuran and tetrahydropyran has been developed under visible light irradiation conditions via radical 1, 2-alkoxyl-trifluoromethylation of unactivated alkene. It features the use of readily commercially available and operatively simple trifluoromethanesulfonyl chloride as a trifluoro- methyl radical source, thus making the protocol potentially appealing for practical preparation.
- trifluoromethanesulfonyl chloride,
- tetrahydrofuran,
- tetrahydropyran,
- visible light,
- alkoxyl-trifluoromethylation
1. [1]
2. [2]
  (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
  (b) Nasir, N. M.; Ermanis, K.; Clarke, P. A. Org. Biomol. Chem. 2014, 12, 3323.
  (c) Tikad, A.; Delbrouck, J. A.; Vincent, S. P. Chem.-Eur. J. 2016, 22, 9456.
3. [3]
  (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
  (b) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
  (c) Zhou, Y.; Wang, J.; Gu, Z.; Wang, S.; Zhu, W.; Aceñ a, J. L.; Soloshonok, V. A.; Izawa, K.; Liu, H. Chem. Rev. 2016, 116, 422.
  (d) Meanwell, N. A. J. Med. Chem. 2018, 61, 5822.
4. [4]
  (a) Jeschke, P. ChemBioChem 2004, 5, 570.
  (b) Jeschke, P. Pest Manage. Sci. 2010, 66, 10.
  (c) Fujiwara, T.; O'Hagan, D. J. Fluorine Chem. 2014, 167, 16.
5. [5]
  Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Blackwell Publishing Ltd, West Sussex, 2009.
6. [6]
7. [7]
  (a) Magueur, G.; Crousse, B.; Charneau, S.; Grellier, P.; Bégué, J.-P.; Bonnet-Delpon, D. J. Med. Chem. 2004, 47, 2694.
  (b) Frezza, M.; Balestrino, D.; Soulère, L.; Reverchon, S.; Queneau, Y.; Forestier, C.; Doutheau, A. Eur. J. Org. Chem. 2006, 2006, 4731.
  (c) Chen, J.-L.; You, Z.-W.; Qing, F.-L. J. Fluorine Chem. 2013, 155, 143.
  (d) Kim, S.; Kim, E.; Lee, W.; Hong, J. H. Nucleosides Nucleotides Nucleic Acids 2014, 33, 747.
  (e) Kollatos, N.; Manta, S.; Dimopoulou, A.; Parmenopoulou, V.; Triantakonstanti, V. V.; Kellici, T.; Mavromoustakos, T.; Schols, D.; Komiotis, D. Carbohydr. Res. 2015, 407, 170.
  (f) Shibata, H.; Tsuchikawa, H.; Hayashi, T.; Matsumori, N.; Murata, M.; Usui, T. Chem.-Asian J. 2015, 10, 915.
  (g) Achmatowicz, M. M.; Allen, J. G.; Bio, M. M.; Bartberger, M. D.; Borths, C. J.; Colyer, J. T.; Crockett, R. D.; Hwang, T.-L.; Koek, J. N.; Osgood, S. A.; Roberts, S. W.; Swietlow, A.; Thiel, O. R.; Caille, S. J. Org. Chem. 2016, 81, 4736.
8. [8]
  (a) Yang, B.; Xu, X.-H.; Qing, F.-L. Chin. J. Chem. 2016, 34, 465.
  (b) Li, T.; Yu, P.; Lin, J.-S.; Zhi, Y.; Liu, X.-Y. Chin. J. Chem. 2016, 34, 490.
9. [9]
  (a) Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462.
  (b) Beniazza, R.; Molton, F.; Duboc, C.; Tron, A.; McClenaghan, N. D.; Lastécouères, D.; Vincent, J.-M. Chem. Commun. 2015, 51, 9571.
  (c) Wang, Y.; Jiang, M.; Liu, J.-T. Adv. Synth. Catal. 2016, 358, 1322.
  (d) Cheng, Y.-F.; Dong, X.-Y.; Gu, Q.-S.; Yu, Z.-L.; Liu, X.-Y. Angew. Chem., Int. Ed. 2017, 56, 8883.
10. [10]
  Noto, N.; Koike, T.; Akita, M. J. Org. Chem. 2016, 81, 7064. doi: 10.1021/acs.joc.6b00953
11. [11]
  (a) Foulard, G.; Brigaud, T.; Portella, C. J. Fluorine Chem. 1998, 91, 179.
  (b) Lin, R.; Sun, H.; Yang, C.; Shen, W.; Xia, W. Chem. Commun. 2015, 51, 399.
  (c) Ryzhakov, D.; Jarret, M.; Guillot, R.; Kouklovsky, C.; Vincent, G. Org. Lett. 2017, 19, 6336.
12. [12]
  (a) Heaton, C. A.; Powell, R. L. J. Fluorine Chem. 1989, 45, 86.
  (b) Kamigata, N.; Fukushima, T.; Yoshida, M. J. Chem. Soc., Chem. Commun. 1989, 1559.
  (c) Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224.
  (d) Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765.
  (e) Chachignon, H.; Guyon, H.; Cahard, D. Beilstein J. Org. Chem. 2017, 13, 2800.
13. [13]
  (a) Yu, P.; Lin, J.-S.; Li, L.; Zheng, S.-C.; Xiong, Y.-P.; Zhao, L.-J.; Tan, B.; Liu, X.-Y. Angew. Chem., Int. Ed. 2014, 53, 11890.
  (b) Yu, P.; Zheng, S.-C.; Yang, N.-Y.; Tan, B.; Liu, X.-Y. Angew. Chem., Int. Ed. 2015, 54, 4041.
  (c) Lin, J.-S.; Dong, X.-Y.; Li, T.-T.; Jiang, N.-C.; Tan, B.; Liu, X.-Y. J. Am. Chem. Soc. 2016, 138, 9357.
  (d) Li, L.; Li, Z.-L.; Wang, F.-L.; Guo, Z.; Cheng, Y.-F.; Wang, N.; Dong, X.-W.; Fang, C.; Liu, J.; Hou, C.; Tan, B.; Liu, X.-Y. Nat. Commun. 2016, 7, 13852.
  (e) Li, L.; Li, Z.-L.; Gu, Q.-S.; Wang, N.; Liu, X.-Y. Sci. Adv. 2017, 3, e1701487.
  (f) Lin, J.-S.; Wang, F.-L.; Dong, X.-Y.; He, W.-W.; Yuan, Y.; Chen, S.; Liu, X.-Y. Nat. Commun. 2017, 8, 14841.
  (g) Li, X.-T.; Gu, Q.-S.; Dong, X.-Y.; Meng, X.; Liu, X.-Y. Angew. Chem., Int. Ed. 2018, 57, 7668.
14. [14]
  (a) Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527.
  (b) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
  (c) Teplý, F. Collect. Czech. Chem. Commun. 2011, 76, 859.
  (d) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828.
  (e) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
  (f) Hopkinson, M. N.; Sahoo, B.; Li, J.-L.; Glorius, F. Chem.-Eur. J. 2014, 20, 3874.
  (g) Koike, T.; Akita, M. Inorg. Chem. Front. 2014, 1, 562.
  (h) Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355.
  (i) Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850.
  (j) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
  (k) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898.
  (l) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116, 10035.
  (m) Staveness, D.; Bosque, I.; Stephenson, C. R. J. Acc. Chem. Res. 2016, 49, 2295.
  (n) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans, R. W.; MacMillan, D. W. C. Nat. Rev. Chem. 2017, 1, 52.
  (o) Cao, M.-Y.; Ren, X.; Lu, Z. Tetrahedron Lett. 2015, 56, 3732.
15. [15]
  (a) Huang, L.; Ye, L.; Li, X.-H.; Li, Z.-L.; Lin, J.-S.; Liu, X.-Y. Org. Lett. 2016, 18, 5284.
  (b) Li, Z.-L.; Li, X.-H.; Wang, N.; Yang, N.-Y.; Liu, X.-Y. Angew. Chem., Int. Ed. 2016, 55, 15100.
  (c) Wang, N.; Li, L.; Li, Z.-L.; Yang, N.-Y.; Guo, Z.; Zhang, H.-X.; Liu, X.-Y. Org. Lett. 2016, 18, 6026.
  (d) Wang, N.; Wang, J.; Guo, Y.-L.; Li, L.; Sun, Y.; Li, Z.; Zhang, H.-X.; Guo, Z.; Li, Z.-L.; Liu, X.-Y. Chem. Commun. 2018, 54, 8885.
16. [16]
  Kim, E.; Choi, S.; Kim, H.; Cho, E. J. Chem.-Eur. J. 2013, 19, 6209. doi: 10.1002/chem.201300564
17. [17]
  (a) Jiang, H.; Huang, C.; Guo, J.; Zeng, C.; Zhang, Y.; Yu, S. Chem.-Eur. J. 2012, 18, 15158.
  (b) Jiang, H.; Cheng, Y.; Zhang, Y.; Yu, S. Eur. J. Org. Chem. 2013, 2013, 5485.
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