Preparation of Diketones via the Reaction of Bisorganozinc Iodides and Benzoyl Chlorides

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (08): 1240-1244. Previous Articles Next Articles

Notes

双有机碘化锌试剂与苯甲酰氯反应制备二酮类化合物的反应

徐长明，杨磊，黄丹凤*，牛腾，傅颖，胡雨来

(西北师范大学化学化工学院甘肃省高分子材料重点实验室兰州 730070)

收稿日期:2009-12-11 修回日期:2010-01-25 发布日期:2010-03-10
通讯作者: 徐长明 E-mail:xuchangming@nwnu.edu.cn

Preparation of Diketones via the Reaction of Bisorganozinc Iodides and Benzoyl Chlorides

XU Chang-Ming, YANG Lei, HUANG Dan-Feng, NIU Teng, FU Ying, HU Yu-Lai

(Gansu key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070)

Received:2009-12-11 Revised:2010-01-25 Published:2010-03-10

Abstract

A series of symmetrical aromatic diketones were synthesized by the coupling reaction of bisorganozinc iodides and acyl chlorides in the presence of cuprous cyanide and lithium chloride in tetrahydrofuran at －25 ℃. The structures of the products were characterized by IR, ¹H NMR, ¹³C NMR, MS techniques and elemental analysis. This method has the advantages of shorter reaction steps, good yields and simple work-up procedures, which is a new and efficient method for synthesis of long chain diketones.

Key words: bisorganozinc iodide reagent, acyl chloride, diketone

Cite this article

XU Chang-Ming, YANG Lei, HUANG Dan-Feng, NIU Teng, FU Ying, HU Yu-Lai. Preparation of Diketones via the Reaction of Bisorganozinc Iodides and Benzoyl Chlorides[J]. Chin. J. Org. Chem., 2010, 30(08): 1240-1244.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Changjun Liu, Huiling Hu, Chenghong Liu, Chaojie Zhu, Tiandi Tang. Pd Supported on Mesoporous ETS-10 Zeolite Catalyst with Superior Catalytic Performances in Synthesizing 1,2-Diones from the Oxidation of Internal Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2953-2960.
[2]	Zhiwei Ma, Xiaopei Chen, Chuanchuan Wang, Jianling Wang, Jingchao Tao, Quanjian Lü. Chiral Squaramide Catalyzed Enantioselective Michael Addition of Cyclic 1,3-Diketones to β,γ-Unsaturated α-Keto Esters [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1520-1526.
[3]	Yuxuan Zhang, Limin Xu, Yan Lu, Zhaoguo Zhang. Progress in Asymmetric Catalytic Reduction of Diketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3221-3239.
[4]	Chaochao Wang, Hui Liu, Wei Zhao, Pan Li, Lusha Ji, Renmin Liu, Kang Lei, Xiaohua Xu. Synthesis and Herbicidal Activity of 5-(1-Amino-2-phenoxyethylidene)barbituric Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2063-2073.
[5]	Zhang Pengpeng, Han Shenghua, Chen Jianxin. Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1737-1744.
[6]	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.
[7]	Dai Xuemei, Li Yanjun, Zhang Shaonan, Gong Lei. Visible-Light-Induced[3+2] Annulation of Cyclopropylamines with 1,2-Diketone Derivatives [J]. Chin. J. Org. Chem., 2019, 39(6): 1711-1719.
[8]	Liu Jiangong, Li Xiaolong, Cheng Xu, Hao Wenmei, Hai Li, Wu Yong. Condensation of 1-(1-Ethyl-1H-indol-5-yl)-2-phenylethane- 1,2-dione to 1,2,4-Triazines [J]. Chin. J. Org. Chem., 2016, 36(2): 370-376.
[9]	Wang Kehu, Yin Xuejiao, Tao Rui, Huang Danfeng, Su Yingpeng, Hu Yulai, Fu Ying, Du Zhengyin, Wang Jinxian. Study on the Grinding-Induced Solvent-Free Preparation of 3-Styryl-1,5-diketones [J]. Chin. J. Org. Chem., 2016, 36(1): 113-120.
[10]	Wang Fengjiao, Lu Ailing, Huang Danfeng, Su Yingpeng, Xia Xiaowen, Xü Yanli, Wang Ke-Hu, Hu Yulai. "One-Pot" Synthesis of Ketones from the Reaction of Weinreb Amides and Halides Prompted by Magnesium Powder [J]. Chin. J. Org. Chem., 2015, 35(5): 1046-1051.
[11]	Zhu Xueyou, Li Xiaohong, Han Fengjiao, Zhang Shichen, Zhao Haiying, Bian Zhanxi. Burning-Rate Catalytic Properties of Ferrocenyl β-Diketones and Their Cu(II), Ni(II) Complexes [J]. Chin. J. Org. Chem., 2015, 35(4): 922-926.
[12]	Li Li, Liu Qingjian, Sui Xueyan. Synthesis of C(5)-(p-Toluoyl substituted)-3,4-dihydropyrimi- dinones (or -thiones) via Biginelli Reaction Promoted with Microwave Irradiation under Solvent-Free Conditions [J]. Chin. J. Org. Chem., 2014, 34(8): 1669-1672.
[13]	Xu Changming, Yang Lei, Huang Danfeng, Niu Teng, Hu Yulai, Wang Kehu . Study on the Coupling Reaction of Fuctionalized Bisorganozinc Iodides and Acyl Chlorides [J]. Chin. J. Org. Chem., 2012, (03): 574-579.
[14]	LIU Xing-Wang, GAO Sai-Sheng-Tai, WANG Li, JIANG Jia-Dong. Synthesis, Characterization and Fluorescence Property of a New β-Diketone and Its Rare Earth Complexes [J]. Chin. J. Org. Chem., 2010, 30(12): 1848-1853.
[15]	LIU Xin-Wang, WANG Na, GAO Sai-Sheng-Tai, GAO Dun-Fang. Synthesis, Luminescent Properties and Theoretical Study of Ternary Complexes of Eu3＋ and Tb3＋ with β-Diketone and 1,10-Phenanthroline [J]. Chin. J. Org. Chem., 2009, 29(10): 1676-1681.

双有机碘化锌试剂与苯甲酰氯反应制备二酮类化合物的反应

Preparation of Diketones via the Reaction of Bisorganozinc Iodides and Benzoyl Chlorides

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments