Citation: Li Qingxue, Li Mengwei, Shi Shaoqing, Ji Xiaoshuang, He Chunlan, Jiang Bo, Hao Wenjuan. PhI(OAc)₂-Mediated Dediazodioxygenation of α-Diazo Carbonyls[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 384-390. doi: 10.6023/cjoc201909041 shu

PhI(OAc)₂-Mediated Dediazodioxygenation of α-Diazo Carbonyls

Li Qingxue ^† ,
Li Mengwei ^† ,
Shi Shaoqing ^† ,
Ji Xiaoshuang ^† ,
He Chunlan ^† ,
Jiang Bo ^, ,
Hao Wenjuan ^,

School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116

Corresponding author: Jiang Bo, jiangchem@jsnu.edu.cn Hao Wenjuan, wjhao@jsnu.edu.cn
Received Date: 30 September 2019
Revised Date: 15 October 2019
Available Online: 1 February 2019
Fund Project: the Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions and the National College Student's Innovation and Entrepreneurship Training Program 201810320156Xthe National Natural Science Foundation of China 21602087Project supported by the National Natural Science Foundation of China (No. 21602087), the Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions and the National College Student's Innovation and Entrepreneurship Training Program (Nos. 201810320156X, 201810320019Z)the Top-Notch Academic Programs Project of Jiangsu Higher Education Institutions and the National College Student's Innovation and Entrepreneurship Training Program 201810320019Z

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A new PhI(OAc)₂-mediated dediazodioxygenation of α-diazo carbonyls was reported. By using the characteristics of the in-situ-generated O-centered radicals from the interaction of PhI(OAc)₂ and N-hydroxy phthalimide (or N-hydroxy succinimide), O-centered radical-triggered dioxygenation of α-diazo carbonyls was achieved in this transformation, which led to the synthesis of a series of α, α-dioxoarylketones and α, α-dioxoesters with moderate to good yields. Based on the experimental results and literature reports, the possible reaction mechanism was proposed, which involved O-centered radical addition, C-N bond homolysis and radical cross coupling. In addition, the reaction featured mild conditions and simple operation without any catalyst.
- dioxygenation,
- dediazotization,
- α, α-dioxoarylketones,
- α, α-dioxoesters
1. [1]
2. [2]
3. [3]
  (a) Clapham, B.; Spanka, C.; Janda, K. D. Org. Lett. 2001, 3, 2173.
  (b) Matsushita, H.; Lee, S.-H.; Yoshida, K.; Clapham, B.; Koch, G.; Zimmermann, J.; Janda, K. D. Org. Lett. 2004, 6, 4627.
4. [4]
5. [5]
  (a) Maas, G. Chem. Soc. Rev. 2004, 33, 183.
  (b) Sambasivanand, R.; Ball, Z. T. Angew. Chem., Int. Ed. 2012, 51, 8568.
  (c) Adly, F. G.; Gardiner, M. G.; Ghanem, A. Chem.-Eur. J. 2016, 22, 3447.
  (d) Qin, C.; Boyarskikh, V.; Hansen, J. H.; Hardcastle, K. I.; Musaev, D. G.; Davies, H. M. L. J. Am. Chem. Soc. 2011, 133, 19198.
  (e) Xu, H.; Li, Y.-P.; Cai, Y.; Wang, G.-P.; Zhu, S. F.; Zhou, Q.-L. J. Am. Chem. Soc. 2017, 139, 7697.
6. [6]
  (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
  (b) Yakura, T.; Ozono, A.; Matsui, K.; Yamashita, M.; Fujiwara, T. Synlett 2013, 24, 65.
  (c) Roberts, E.; Sançon, J. P.; Sweeney, J. B. Org. Lett. 2005, 7, 2075.
7. [7]
  (a) Neupane, P.; Li, X.; Jung, J. H.; Lee, Y. R.; Kim, S. H. Tetrahedron 2012, 68, 2496.
  (b) Dyer, J.; Jockusch, S.; Balsanek, V.; Sames, D.; Turro, N. J. Org. Chem. 2005, 70, 2143.
  (c) Dussault, P. H.; Xu, C. Tetrahedron Lett. 2004, 45, 7455.
8. [8]
  (a) Wang, N.-N.; Huang, L.-R.; Hao, W.-J.; Zhang, T.-S.; Li, G.; Tu, S.-J.; Jiang, B. Org. Lett. 2016, 18, 1298.
  (b) Hao, W.-J.; Gao, Q.; Jiang, B.; Liu, F.; Wang, S.-L.; Tu, S.-J.; Li, G. J. Org. Chem. 2016, 81, 11276.
  (c) Wang, N.-N.; Hao, W.-J.; Zhang, T.-S.; Li, G.; Wu, Y.-N.; Tu, S.-J.; Jiang, B. Chem. Commun. 2016, 52, 5144.
  (d) Zhang, T.-S.; Hao, W.-J.; Wang, N.-N.; Li, G.; Jiang, D.-F.; Tu, S.-J.; Jiang, B. Org. Lett. 2016, 18, 3078.
  (e) Zhang, T.-S.; Zhang, H.; Fu, R.; Wang, J.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Chem. Commun. 2019, 55, 13231.
9. [9]
10. [10]
11. [11]
  (a) Lu, H.; Dzik, W. I.; Xu, X.; Wojtas, L.; de Bruin, B.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 8518.
  (b) Zheng, J.; Qi, J.; Cui, S. J. Org. Chem. 2015, 80, 9224.
  (c) Jiang, J.; Liu, J.; Yang, L.; Shao, Y.; Cheng, J.; Bao, X.; Wan, X. Chem. Commun. 2015, 51, 14728.
12. [12]
  Zhang, J.; Jiang, J.; Xu, D.; Luo, Q.; Wang, H.; Chen, J.; Li, H.; Wang, Y.; Wan, X. Angew. Chem., Int. Ed. 2015, 54, 1231. doi: 10.1002/anie.201408874
13. [13]
  Wang, N.-N.; Hao, W.-J.; Zhang, T.-S.; Li, G.; Wu, Y.-N.; Tu, S.-J.; Jiang, B. Chem. Commun. 2016, 52, 5144. doi: 10.1039/C6CC00816J
14. [14]
1. [1]
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19. [19]
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PhI(OAc)₂-Mediated Dediazodioxygenation of α-Diazo Carbonyls