Citation: Chen Cui, Qiu Huihua. Study on the α-Acetoxylation of sp³-C-H Bonds Adjacent to Carbonyl of Arones[J]. Chinese Journal of Organic Chemistry, ;2016, 36(4): 826-829. doi: 10.6023/cjoc201510011 shu

Study on the α-Acetoxylation of sp³-C-H Bonds Adjacent to Carbonyl of Arones

Chen Cui ^, ,
Qiu Huihua

1.
College of Chemcal Engineering, Guangdong University of Petrochemical Technology, Maoming 525000

Corresponding author: Chen Cui,
Received Date: 12 October 2015
Available Online: 21 November 2015
Fund Project: 广东省优秀青年基金(No.2013LYM_0059)资助项目. (No.2013LYM_0059)

In this work, an efficient α-acetoxylation of sp³-C-H bonds adjacent to carbonyl of arones to construct α-acetoxy acetophenone derivatives was developed. The influences of reaction time, copper salts, iodine and the loading of copper salts and iodine on this transformation were investigated, and the optimal reaction conditions were also obtained. In addition, a possible reaction mechanism was proposed. This protocol with its advantages of simple procedure and high yield provides a novel valuable approach to α-acetoxy acetophenones.
- acetophenone,
- sp³-C-H bond,
- acetoxylation,
- α-acetoxy acetophenone
1. [1]
  [1] Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193.
2. [2]
  [2] Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177
3. [3]
  [3] Zhu, C.; Yang, B.; Bäckvall, J. E. J. Am. Chem. Soc. 2015, 137, 11868.
4. [4]
  [4] Henrion, M.; Ritleng, V.; Chetcuti, M. J. ACS Catal. 2015, 5, 1283.
5. [5]
  [5] Zhang, Y.; Feng, B. N. Chin. J. Org. Chem. 2014, 34, 2406 (in Chinese). (张艳, 冯柏年, 有机化学, 2014, 34, 2406.)
6. [6]
  [6] Chen, T. B.; Zhang, M. Chin. J. Org. Chem. 2015, 35, 813 (in Chinese). (陈天保, 章明, 有机化学, 2015, 35, 813.)
7. [7]
  [7] Ni, C. F.; Zhu, L. G.; Hu, J. B. Acta Chim. Sinica 2015, 73, 90 (in Chinese). (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.)
8. [8]
  [8] Liu, J.; Zhu, Q. R.; Du, J. A.; Zhang, X. L. Chin. J. Org. Chem. 2015, 35, 15 (in Chinese). (刘杰, 朱庆仁, 杜娟, 张袖丽, 有机化学, 2015, 35, 15.)
9. [9]
  [9] Gang, F. L.; Xu, G. L.; Dong, T. S.; Yang, L.; Du, Z. Y. Chin. J. Org. Chem. 2015, 35, 1428 (in Chinese). (刚芳莉, 徐光利, 董涛生, 杨丽, 杜正银, 有机化学, 2015, 35, 1428.)
10. [10]
  [10] Wu, J. L.; Xiang, H. H.; Zeng, J.; Leow, M. L.; Liu, X. W. Org. Lett. 2015, 17, 222.
11. [11]
  [11] Gurram, V.; Akula, H. K.; Garlapati1, R.; Pottabathini, N.; Lakshman, M. K. Adv. Synth. Catal. 2015, 357, 451.
12. [12]
  [12] Tang, C. H.; Jiao, N. Angew. Chem., Int. Ed. 2014, 53, 6528.
13. [13]
  [13] Greenhalgh, M. D.; Frank, D. J.; Thomas, S. P. Angew. Chem., Int. Ed. 2014, 356, 584.
14. [14]
  [14] Green, R. A.; Hartwig, J. F. Angew. Chem., Int. Ed. 2015, 54, 3768.
15. [15]
  [15] Reid, E. B.; Fortenbauch, R. B.; Patterson, H. R. J. Org. Chem. 1950, 15, 579.
16. [16]
  [16] Shindo, M.; Yoshimura, Y.; Hayashi, M.; Soejima, H.; Yoshikawa, T.; Matsumoto, K.; Shishido, K. Org. Lett. 2007, 9, 1963.
17. [17]
  [17] Lee, J. C.; Jin, Y. S.; Choi, J. H. Chem. Commun. 2001, 956.
18. [18]
  [18] Ochiai, M.; Takeuchi, Y.; Katayama, T.; Sueda, T.; Miyamoto, K. J. Am. Chem. Soc. 2005, 127, 12244.
19. [19]
  [19] Demir, A. S.; Hamamci, H.; Tanyeli, C.; Akhmedov, I. M.; Doganel, F. Tetrahedron: Asymmetry 1998, 9, 1673.
20. [20]
  [20] Sheng, J. M.; Li, X. L.; Tang, M. F.; Gao, B. T.; Huang, G. S. Synthesis 2007, 1165.
21. [21]
  [21] Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331.
22. [22]
  [22] Cort, A. D. J. Org. Chem. 1991, 56, 6708.
23. [23]
  [23] Yin, G. D.; Gao, M.; She, N. F.; Hu, S. L.; Wu, A. X.; Pan, Y. J. Synthesis 2007, 3113.
24. [24]
  [24] Wang, Z. H.; Yin, G. D.; Qin, J.; Gao, M.; Cao, L. P.; Wu, A. X. Synthesis 2008, 3675.
25. [25]
  [25] Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331.
26. [26]
  [26] Anastasaki, A.; Nikolaou, V.; Zhang, Q.; Burns, J.; Samanta, S. R.; Waldron, C.; Haddleton, A. J.; McHale, R.; Fox, D.; Percec, V.; Wilson, P.; Haddleton, D. M. J. Am. Chem. Soc. 2014, 136, 1141.
27. [27]
  [27] Tan, L. Q.; Liu, W. B.; Huang, M.; Yu, M. Chin. J. Org. Chem. 2014, 34, 817 (in Chinese). (谭丽泉, 刘卫兵, 黄敏, 于梅, 有机化学, 2014, 34, 817.)
28. [28]
  [28] Percec, V.; Guliashvili, T.; Ladislaw, J. S.; Wistrand, A.; Stjerndahl, A.; Sienkowska, M. J.; Monteiro, M. J.; Sahoo, S. J. Am. Chem. Soc. 2006, 128, 14156.
29. [29]
  [29] Walker, E. H.; Apblett, A. W.; Walker, R.; Zachary, A. Chem. Mater. 2004, 16, 5336.
30. [30]
  [30] Xu, Y. H.; Lu, J.; Loh, T. P. J. Am. Chem. Soc. 2009, 131, 1372.
31. [31]
  [31] Shirai, M.; Mitsukura, K.; Okamura, H. Chem. Mater. 2008, 20, 1971.
1. [1]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
2. [2]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
3. [3]
  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
4. [4]
  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
5. [5]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
6. [6]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
7. [7]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
8. [8]
  Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
9. [9]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
10. [10]
  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
11. [11]
  Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp³)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
12. [12]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
13. [13]
  Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp³)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
14. [14]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
15. [15]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
16. [16]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
17. [17]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
18. [18]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
19. [19]
  Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp³)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
20. [20]
  Jianfeng Yan , Yating Xiao , Xin Zuo , Caixia Lin , Yaofeng Yuan . Comprehensive Chemistry Experimental Design of Ferrocenylphenyl Derivatives. University Chemistry, 2024, 39(4): 329-337. doi: 10.3866/PKU.DXHX202310005

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(724)
HTML views(75)

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

Study on the α-Acetoxylation of sp3-C-H Bonds Adjacent to Carbonyl of Arones

Metrics

通讯作者: 陈斌, bchen63@163.com

Study on the α-Acetoxylation of sp³-C-H Bonds Adjacent to Carbonyl of Arones