Citation: Guo Zhen, Xie Mingsheng, Han Ruijie, Qu Guirong, Guo Haiming. Ag-Catalyzed Monofluoromethylation of Purin-9-yl Allenes with Fluorobis(phenylsulfonyl)methane[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 112-117. doi: 10.6023/cjoc201711001 shu

Ag-Catalyzed Monofluoromethylation of Purin-9-yl Allenes with Fluorobis(phenylsulfonyl)methane

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007

Corresponding author: Qu Guirong, quguir@sina.com Guo Haiming, ghm@htu.edu.cn
Received Date: 1 November 2017
Revised Date: 19 November 2017
Available Online: 21 January 2017
Fund Project: the Program of Introducing Talents of Discipline to Universities D17007the Plan for Scientific Innovation Talent of Henan Province 164200510008the National Natural Science Foundation of China 21402041the Program of Introducing Talents of Discipline to Universities 111计划the National Natural Science Foundation of China U1604283Project supported by the National Natural Science Foundation of China (Nos. U1604283, 21402041), the Plan for Scientific Innovation Talent of Henan Province (No. 164200510008), the China Postdoctoral Science Foundation Funded Project (No. 2016M592293), the Program for Innovative Research Team in Science, Technology in University of Henan Province (No. 15IRTSTHN003) and the Program of Introducing Talents of Discipline to Universities (111 Project, No. D17007)the Program for Innovative Research Team in Science, Technology in University of Henan Province 15IRTSTHN003the China Postdoctoral Science Foundation Funded Project 2016M592293

Figures(4)

The monofluoromethylation of purin-9-yl allenes with fluorobis(phenylsulfonyl)methane has been achieved. With AgF (3 mol%) as the catalyst, the fluorobis(phenylsulfonyl)methylated adducts could be afforded in excellent yields. The monofluoromethylation exhibited high chemoselectivities and E-selectivies. Meanwhile, the monofluoromethylation of purin-9-yl allenes with fluorobis(phenylsulfonyl)methane provided a useful route to construct fluorinated acyclic nucleoside analogues.
- monofluoromethylation,
- purin-9-yl allene,
- fluorobis(phenylsulfonyl)methane
1. [1]
  (a) Smart, B. E. J. Fluorine Chem. 2001, 109, 3.
  (b) Kirsch, P. Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, Germany, 2004.
  (c) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013.
  (d) Li, Y.; Ni, C.; Liu, J.; Zhang, L.; Zheng, J.; Zhu, L.; Hu, J. Org. Lett. 2006, 8, 1693.
  (e) Bégué, J.-P.; Bonnet-Delpon, D. J. Fluorine Chem. 2006, 127, 992.
  (f) Prakash, G. K. S.; Hu, J. Acc. Chem. Res. 2007, 40, 921.
  (g) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
  (h) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
  (i) Hu, J.; Zhang, W.; Wang, F. Chem. Commun. 2009, 7465.
  (j) Liao, F.-M.; Yu, J.-S.; Zhou, J. Chin. J. Org. Chem. 2017, 37, 2175(in Chinese).(廖富民, 余金生, 周剑, 有机化学, 2017, 37, 2175.)
  (k) Liao, F.-M.; Cao, Z.-Y.; Yu, J.-S.; Zhou, J. Angew. Chem., Int. Ed. 2017, 56, 2459.
2. [2]
  Fukuzumi, T.; Shibata, N.; Sugiura, M.; Yasui, H.; Nakamura, S.; Toru, T. Angew. Chem., Int. Ed. 2006, 45, 4973 doi: 10.1002/(ISSN)1521-3773
3. [3]
  Ni, C.; Li, Y.; Hu, J. J. Org. Chem. 2006, 71, 6829. doi: 10.1021/jo060955l
4. [4]
  Prakash, G. K. S.; Chacko, S.; Alconcel, S.; Stewart, T.; Mathew, T.; Olah, G. A. Angew. Chem., Int. Ed. 2007, 46, 4933. doi: 10.1002/(ISSN)1521-3773
5. [5]
  (a) Furukawa, T. ; Goto, Y. ; Kawazoe, J. ; Tokunaga, E. ; Naka-mura, S. ; Yang, Y. ; Du, H. ; Kakehi, A. ; Shiro, M. ; Shibata, N. Angew. Chem., Int. Ed. 2010, 49, 1642.
  (b) Prakash, G. K. S. ; Shao, N. ; Zhang, Z. ; Ni, C. ; Wang, F. ; Haiges, R. ; Olah, G. A. J. Fluorine Chem. 2012, 133, 27.
  (c) Shen, X. ; Miao, W. ; Ni, C. ; Hu, J. Angew. Chem., Int. Ed. 2014, 53, 775.
6. [6]
  (a) Liu, W. -B. ; Zheng, S. -C. ; He, H. ; Zhao, X. -M. ; Dai, L. -X. ; You, S. -L. Chem. Commun. 2009, 6604.
  (b) Furukawa, T. ; Kawazoe, J. ; Zhang, W. ; Nishimine, T. ; Tokunaga, E. ; Matsumoto, T. ; Shiro, M. ; Shibata, N. Angew. Chem., Int. Ed. 2011, 50, 9684.
  (c) Yang, W. ; Wei, X. ; Pan, Y. ; Lee, R. ; Zhu, B. ; Liu, H. ; Yan, L. ; Huang, K. -W. ; Jiang, Z. ; Tan, C. -H. Chem. Eur. J. 2011, 17, 8066.
7. [7]
  (a) Shen, X. ; Zhang, L. ; Zhao, Y. ; Zhu, L. ; Li, G. ; Hu, J. Angew. Chem., Int. Ed. 2011, 50, 2588.
  (b) Ma, H. ; Matsuzaki, K. ; Yang, Y. -D. ; Tokunaga, E. ; Nakane, D. ; Ozawa, T. ; Masuda, H. ; Shibata, N. Chem. Commun. 2013, 49, 11206.
  (c) Shen, X. ; Ni, C. ; Hu, J. Chin. J. Chem. 2013, 31, 878.
  (d) Mizuta, S. ; Shibata, N. ; Goto, Y. ; Furukawa, T. ; Nakamura, S. ; Toru, T. J. Am. Chem. Soc. 2007, 129, 6394.
  (e) Prakash, G. K. S. ; Gurung, L. ; Jog, P. V. ; Tanaka, S. ; Thomas, T. E. ; Ganesh, N. ; Haiges, R. ; Mathew, T. ; Olah, G. A. Chem. Eur. J. 2013, 19, 3579.
8. [8]
  (a) Furukawa, T. ; Shibata, N. ; Mizuta, S. ; Nakamura, S. ; Toru, T. ; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 8051.
  (b) Zhang, S. ; Zhang, Y. ; Ji, Y. ; Li, H. ; Wang, W. Chem. Commun. 2009, 4886.
  (c) Alba, A. -N. ; Companyó, X. ; Moyano, A. ; Rios, R. Chem. Eur. J. 2009, 15, 7035.
  (d) Moon, H. W. ; Cho, M. J. ; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4896.
  (e) Ullah, F. ; Zhao, G. -L. ; Deiana, L. ; Zhu, M. ; Dziedzic, P. ; Ibrahem, I. ; Hammar, P. ; Sun, J. ; Córdova, A. Chem. Eur. J. 2009, 15, 10013.
9. [9]
  Ni, C.; Zhang, L.; Hu, J. J. Org. Chem. 2008, 73, 5699. doi: 10.1021/jo702479z
10. [10]
  hen, X.; Zhang, W.; Zhang, L.; Luo, T.; Wan, X.; Gu, Y.; Hu, J. Angew. Chem., Int. Ed. 2012, 51, 6966. doi: 10.1002/anie.201202451
11. [11]
  Ogasawara, M.; Murakami, H.; Furukawa, T.; Takahashi, T.; Shibata, N. Chem. Commun. 2009, 7366.
12. [12]
  (a) Baszczyňski, O. ; Zaneba, Z. Med. Res. Rev. 2013, 33, 1304.
  (b) Jindřich, J. ; Hol, A. ; Dvořáková, H. Collect. Czech. Chem. Commun. 1993, 58, 1645.
  (c) Kiesewetter, D. O. ; Knudson, K. ; Collins, M. ; Srinivasula, S. ; Lim, E. ; Mascio, M. D. J. Labelled Compd. Radiopharm. 2008, 51, 187.
13. [13]
  (a) Liang, L. ; Xie, M. -S. ; Wang, H. -X. ; Niu, H. -Y. ; Qu, G. -R. ; Guo, H. -M. J. Org. Chem. 2017, 82, 5966.
  (b) Liang, L. ; Xie, M. -S. ; Qin, T. ; Zhu, M. ; Qu, G. -R. ; Guo, H. -M. Org. Lett. 2017, 19, 5212.
  (c) Sun, H. -L. ; Chen, F. ; Xie, M. -S. ; Guo, H. -M. ; Qu, G. -R. ; He, Y. -M. ; Fan, Q. -H. Org. Lett. 2016, 18, 2260.
  (d) Zhang, D. -J. ; Xie, M. -S. ; Qu, G. -R. ; Gao, Y. -W. ; Guo, H. -M. Org. Lett. 2016, 18, 820.
  (e) Xie, M. -S. ; Wang, Y. ; Li, J. -P. ; Du, C. ; Zhang, Y. -Y. ; Hao, E. -J. ; Zhang, Y. -M. ; Qu, G. -R. ; Guo, H. -M. Chem. Commun. 2015, 51, 12451.
  (f) Niu, H. -Y. ; Du, C. ; Xie, M. -S. ; Wang, Y. ; Zhang, Q. ; Qu, G. -R. ; Guo, H. -M. Chem. Commun. 2015, 51, 3328.
  (g) Wei, T. ; Xie, M. -S. ; Qu, G. -R. ; Niu, H. -Y. ; Guo, H. -M. Org. Lett. 2014, 16, 900.
14. [14]
  For reviews about synthesis of acyclic nucleoside analogues, see: (a) Xie, M. -S. ; Niu, H. -Y. ; Qu, G. -R. ; Guo, H. -M. Tetrahedron Lett. 2014, 55, 7156.
  (b) Guo, H. -M. ; Wu, S. ; Niu, H. -Y. ; Song, G. ; Qu, G. -R. In Chemical Synthesis of Nucleoside Analogues, Ed. : Merino, P., John Wiley & Sons, Hoboken, New Jersey, 2013, p. 103.
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