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

Figures(4)

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]
  Bolin Sun , Jie Chen , Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032
2. [2]
  Hongting Yan , Aili Feng , Rongxiu Zhu , Lei Liu , Dongju Zhang . Reexamination of the Iodine-Catalyzed Chlorination Reaction of Chlorobenzene Using Computational Chemistry Methods. University Chemistry, 2025, 40(3): 16-22. doi: 10.12461/PKU.DXHX202403010
3. [3]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
4. [4]
  Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
5. [5]
  Ruitong Zhang , Zhiqiang Zeng , Xiaoguang Zhang . Improvement of Ethyl Acetate Saponification Reaction and Iodine Clock Reaction Experiments. University Chemistry, 2024, 39(8): 197-203. doi: 10.3866/PKU.DXHX202312004
6. [6]
  Aili Feng , Xin Lu , Peng Liu , Dongju Zhang . Computational Chemistry Study of Acid-Catalyzed Esterification Reactions between Carboxylic Acids and Alcohols. University Chemistry, 2025, 40(3): 92-99. doi: 10.12461/PKU.DXHX202405072
7. [7]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
8. [8]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
9. [9]
  Shuying Zhu , Shuting Wu , Ou Zheng . Improvement and Expansion of the Experiment for Determining the Rate Constant of the Saponification Reaction of Ethyl Acetate. University Chemistry, 2024, 39(4): 107-113. doi: 10.3866/PKU.DXHX202310117
10. [10]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . Optimizing interfacial electric fields in carbon nitride nanosheet/spherical conjugated polymer S-scheme heterojunction for hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-0. doi: 10.1016/j.actphy.2025.100095
11. [11]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
12. [12]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
13. [13]
  Yiling Wu , Peiyao Jin , Shenyue Tian , Ji Zhang . The Star of Sugar Substitutes: An Interview of Erythritol. University Chemistry, 2024, 39(9): 22-27. doi: 10.12461/PKU.DXHX202404034
14. [14]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
15. [15]
  Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
16. [16]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
17. [17]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
18. [18]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
19. [19]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
20. [20]
  Zhi Chai , Huashan Huang , Xukai Shi , Yujing Lan , Zhentao Yuan , Hong Yan . Wittig反应的立体选择性. University Chemistry, 2025, 40(8): 192-201. doi: 10.12461/PKU.DXHX202410046

Get Citation

PDF

XML

Metrics

PDF Downloads(29)
Abstract views(2915)
HTML views(484)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

Metrics

通讯作者: 陈斌, bchen63@163.com

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