α-Acetoxylation of Aromatic Ketones Mediated by Iodobenzene Diacetate

doi:10.6023/cjoc201311024

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (4): 817-820.DOI: 10.6023/cjoc201311024 Previous Articles Next Articles

Notes

二醋酸碘苯促进的芳酮类化合物羰基邻位乙酰化反应研究

谭丽泉, 刘卫兵, 黄敏, 余梅

广东石油化工学院化学与生命科学学院茂名 525000

收稿日期:2013-11-13 修回日期:2013-12-14 发布日期:2014-01-02
通讯作者: 谭丽泉 E-mail:touching522@163.com
基金资助:
广东省自然科学基金（No. S2012040007868）资助项目

α-Acetoxylation of Aromatic Ketones Mediated by Iodobenzene Diacetate

Tan Liquan, Liu Weibing, Huang Min, Yu Mei

School of Chemistry and Life Science, Guangdong University of Petrochemical Technology, Maoming 525000

Received:2013-11-13 Revised:2013-12-14 Published:2014-01-02
Supported by:
Project supported by the Natural Science Foundation of Guangdong Provine (No. S2012040007868).

This paper reports a simple method for the synthesis of α-acetoxyacetophenone derivatives from acetophenones using ZnO as a catalyst and iodobenzene diacetate as an oxidant. This transformation undergoes two processes: the oxidation of saturated sp³-C—H bond and the acetoxylation of C=C bond. The structures of products were confirmed by IR, ¹H NMR and ¹³C NMR. In addition, a possible reaction mechanism was proposed.

Key words: iodobenzene diacetate, acetophenones, oxidation of saturated sp³-C—H bond, acetoxylation

Cite this article

Tan Liquan, Liu Weibing, Huang Min, Yu Mei. α-Acetoxylation of Aromatic Ketones Mediated by Iodobenzene Diacetate[J]. Chin. J. Org. Chem., 2014, 34(4): 817-820.

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[1]	Bao Kun, Wei Jun, Sheng Rong. Synthesis of α,α,γ,γ-Tetrafluoro-β-hydroxy Ketones and α-Fluoroacetophenones via 1,3-Diaryl-1,3-diketones [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 930-937.
[2]	Ju Chenyang, Wu Zhengxing, Li Yunyi, Zhang Wanbin. Palladium(II)-Catalyzed Aerobic 1,2-Diacetoxylation of Conjugated Dienes [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3925-3933.
[3]	Wang Ligeng, Yu Qin, Feng Chun, Zhang Yan, Hu Jun. Efficient Synthesis of Dibromoalkanes and Iodoacetates from Olefins Using ZnAl-XO₃^--LDHs/LiX (X=Br, I) as Halogen Sources [J]. Chin. J. Org. Chem., 2019, 39(6): 1787-1793.
[4]	Chen Cui, Qiu Huihua. Study on the α-Acetoxylation of sp³-C-H Bonds Adjacent to Carbonyl of Arones [J]. Chin. J. Org. Chem., 2016, 36(4): 826-829.
[5]	Li Ming, Ning Jiabin, Yu Le, Wen Lirong. Copper-Promoted Synthesis of Thiochromones Derivatives [J]. Chin. J. Org. Chem., 2016, 36(11): 2715-2722.
[6]	Chen Tianbao, Zhang Ming. Palladium-Catalyzed C—H Acetoxylation Reations [J]. Chin. J. Org. Chem., 2015, 35(4): 813-826.
[7]	Zhu Wei, Li Zhongzhou, Yao Lulu, Zheng Zubiao, Zou Xinzhuo. One-Pot α-Nucleophilic Fluorination of Acetophenones by DBDMH and Et₃N·3HF [J]. Chin. J. Org. Chem., 2012, 32(06): 1146-1149.
[8]	TIAN Mi, WANG Xiao-Ke. Iodobenzene Diacetate Assisted Synthesis of Benzimidazole Derivatives [J]. Chin. J. Org. Chem., 2009, 29(10): 1654-1658.

二醋酸碘苯促进的芳酮类化合物羰基邻位乙酰化反应研究

α-Acetoxylation of Aromatic Ketones Mediated by Iodobenzene Diacetate

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