Citation: Li Xubin, Zhou Chen, Liu Xingtong, Wang Teng, Yu Xinhong, Ma Hongmei, Li Cuiqing. ipso-Oxidation of Allyl Ether/Decarboxylative Aromatization Cascade Strategy via Oxocarbenium Activation: A Novel Approach for Synthesis of N-Alkyl Pyrroles[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2906-2911. doi: 10.6023/cjoc201904036 shu

ipso-Oxidation of Allyl Ether/Decarboxylative Aromatization Cascade Strategy via Oxocarbenium Activation: A Novel Approach for Synthesis of N-Alkyl Pyrroles

Li Xubin ^a ,
Zhou Chen ^a ,
Liu Xingtong ^a ,
Wang Teng ^b ,
Yu Xinhong ^a,, ,
Ma Hongmei ^a,, ,
Li Cuiqing ^b,,

a.
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, State Key Laboratory of Bioengineering Reactors, School of Pharmacy, East China University of Science & Technology, Shanghai 200237
b.
College of Chemical Engineering, Beijing Institute of Petrochemical Technology, Beijing 102617

Corresponding author: Yu Xinhong, xhyu@ecust.edu.cn Ma Hongmei, hmma@ecust.edu.cn Li Cuiqing, licuiqing@bipt.edu.cn
Received Date: 13 April 2019
Revised Date: 7 May 2019
Available Online: 28 October 2019
Fund Project: the National Natural Science Foundation of China 21476078the Science and Technology Commission of Shanghai Municipality 12431900902Project supported by the National Natural Science Foundation of China (No. 21476078) and the Science and Technology Commission of Shanghai Municipality (No. 12431900902)

Figures(3)

An ipso-oxidation of allyl ether/decarboxylative aromatization cascade strategy is reported, resulting in the formation of N-alkyl pyrroles via oxocarbenium activation. This transformation, which involves formation of C-N bond and cleavage of C-O bond, provides a novel protocol that furnishes N-alkyl pyrroles in 29%~71% yields with good functional group tolerance.
- oxidation of ether,
- aromatization,
- pyrroles,
- synthetic methods
1. [1]
  Curran, D.; Grimshaw, J.; Perera, S. D. Chem. Soc. Rev. 1991, 20, 391. doi: 10.1039/cs9912000391
2. [2]
  (a) Azizian, J.; Karimi, A. R.; Kazemizadeh, Z.; Mohammadi, A. A.; Mohammadizadeh, M. R. J. Org. Chem. 2005, 70, 1471.
  (b) Meshram, H. M.; Prasad, B. R. V.; Aravind Kumar, D. Tetrahedron Lett. 2010, 51, 3477.
  (c) Deb, I.; Coiro, D. J.; Seidel, D. Chem. Commun. 2011, 47, 6473.
  (d) Mao, H.; Wang, S.; Yu, P.; Lv, H.; Xu, R.; Pan, Y. J. Org. Chem. 2011, 76, 1167.
  (e) Zou, Z.; Deng, Z.; Yu, X.; Zhang, M.; Zhao, S.; Luo, T.; Yin, X.; Xu, H.; Wang, W. Sci. China Chem. 2012, 55, 43.
  (f) Satish, G.; Reddy, K. H. V.; Ramesh, K.; Kumar, B. S. P. A.; Nageswar, Y. V. D. Tetrahedron Lett. 2014, 55, 2596.
3. [3]
  (a) Miller, A. J. M.; Kaminsky, W.; Goldberg, K. I. Organometallics 2014, 33, 1245.
  (b) Song, Z.-Z.; Gong, J.-L.; Zhang, M.; Wu, X.-F. Asian J. Org. Chem. 2012, 1, 214.
  (c) Shen, Z.; Dai, J.; Xiong, J.; He, X.; Mo, W.; Hu, B.; Sun, N.; Hu, X. Adv. Synth. Catal. 2011, 353, 3031.
4. [4]
  (a) Zhang, Y.; Li, C.-J. Angew. Chem., Int. Ed. 2006, 45, 1949.
  (b) Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242.
  (c) Tu, W.; Liu, L.; Floreancig, P. E. Angew. Chem., Int. Ed. 2008, 47, 4184.
  (d) Tu, W.; Floreancig, P. E. Angew. Chem., Int. Ed. 2009, 48, 4567.
  (e) Liu, L.; Floreancig, P. E. Angew. Chem., Int. Ed. 2010, 49, 5894.
  (f) Richter, H.; Rohlmann, R.; García Mancheño, O. Chem.-Eur. J. 2011, 17, 11622.
  (g) Muramatsu, W.; Nakano, K.; Li, C.-J. Org. Lett. 2013, 15, 3650.
  (h) Meng, Z.; Sun, S.; Yuan, H.; Lou, H.; Liu, L. Angew. Chem. Int. Ed. 2014, 53, 543.
  (i) Chen, W.; Xie, Z.; Zheng, H.; Lou, H.; Liu, L. Org. Lett. 2014, 16, 5988.
  (j) Yu, B.; Jiang, T.; Li, J.; Su, Y.; Pan, X.; She, X. Org. Lett. 2009, 11, 3442.
  (k) Liu, L.; Floreancig, P. E. Org. Lett. 2010, 12, 4686.
  (l) Liu, X.; Sun, B.; Xie, Z.; Qin, X.; Liu, L.; Lou, H. J. Org. Chem. 2013, 78, 3104.
  (m) Sun, K.; Wang, X.; Li, G.; Zhu, Z.; Jiang, Y.; Xiao, B. Chem. Commun. 2014, 50, 12880.
  (n) Pandit, R. P.; Lee, Y. R. Adv. Synth. Catal. 2014, 356, 3171.
5. [5]
  (a) Reisman, S. E.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2008, 130, 7198.
  (b) McQuaid, K. M.; Sames, D. J. Am. Chem. Soc. 2009, 131, 402.
  (c) Maity, P.; Srinivas, H. D.; Watson, M. P. J. Am. Chem. Soc. 2011, 133, 17142.
  (d) Chen, Y.; Chen, M.; Liu, Y. Angew. Chem. 2012, 124, 6599.
  (e) Rueping, M.; Volla, C. M. R.; Atodiresei, I. Org. Lett. 2012, 14, 4642.
  (f) Lu, C.; Su, X.; Floreancig, P. E. J. Org. Chem. 2013, 78, 9366.
  (g) Srinivas, H. D.; Maity, P.; Yap, G. P. A.; Watson, M. P. J. Org. Chem. 2015, 80, 4003.
  (h) Kong, A.; Andreansky, E. S.; Blakey, S. B. J. Org. Chem. 2017, 82, 4477.
  (i) Fan, W.-T.; Li, N.-K.; Xu, L.; Qiao, C.; Wang, X.-W. Org. Lett. 2017, 19, 6626.
  (j) Lee, S.; Kaib, P. S. J.; List, B. J. Am. Chem. Soc. 2017, 139, 2156.
6. [6]
  (a) Zhang, S.-Y.; Zhang, F.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2011, 40, 1937.
  (b) Morales-Rivera, C. A.; Floreancig, P. E.; Liu, P. J. Am. Chem. Soc. 2017, 139, 17935.
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