Cesium Carbonate Catalyzed Iodination of Terminal Alkynes to Synthesize 1-Iodoalkynes

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Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (05): 663-665. Previous Articles Next Articles

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碳酸铯催化下端炔碘化合成炔基碘

贺干武^a,b，刘凤伟^a，许新华*^,a

(^a湖南大学化学化工学院长沙 410082)
(^b邵阳学院化学与生物技术系邵阳 422400)

收稿日期:2006-01-18 修回日期:2006-10-13 发布日期:2007-05-10
通讯作者: 许新华

Cesium Carbonate Catalyzed Iodination of Terminal Alkynes to Synthesize 1-Iodoalkynes

HE Gan-Wu^a,b, LIU Feng-Wei^a, XU Xin-Hua*^,a

(^aCollege of Chemistry and Chemical Engineering, Hunan University, Changsha 410082)
(^bDepartment of Chemistry and Biotechnogy, Shaoyang University, Shaoyang 422400)

Received:2006-01-18 Revised:2006-10-13 Published:2007-05-10

Contact: XU Xin-Hua

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Abstract

A mixture of cesium carbonate (0.2 equiv.), potassium hydroxide (2.0 equiv.) and terminal al-kynes (1.0 equiv.) in THF-HMPA was stirred at room temperature for 3 h, then the solution of iodine in THF was added and stirred at room temperature for 2 h. The 1-iodoalkynes were obtained in 70%～93% yields.

Key words: terminal alkyne, 1-iodoalkyne, potassium hydroxide, cesium carbonate

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HE Gan-Wu,b, LIU Feng-Wei^a, XU Xin-Hua*^,a. Cesium Carbonate Catalyzed Iodination of Terminal Alkynes to Synthesize 1-Iodoalkynes[J]. Chin. J. Org. Chem., 2007, 27(05): 663-665.

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[1]	Fei Chen, Sheng Tao, Ning Liu, Bin Dai. CNN-Type Binuclear Cu(I) Complexes Catalyzed Direct Carboxylation via the Fixation of CO₂ at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2471-2480.
[2]	Liwen Ma, Xiaoye Wei, Zilin Zhao, Ang Zhao, Xiangwen Deng, Bingnan Huo, Gang Ma, Chunfang Zhang. Theoretical Study on the Catalytic Mechanism of Copper with Various Valence for the Terminal Alkyne Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1811-1819.
[3]	Yinyin Wang, Xiaowan Lin, Piao Zhang, Meihua Shen, Huadong Xu, Defeng Xu. Design and Synthesis of Pyridine and 1,3,5-Triazine PNP Pincer Ligands and Their Application in Cobalt Catalyzed Semihydrogenation of Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3312-3320.
[4]	Jingru Liang, Bingying Wang, Chengyin Huang, Xiaojun Ye, Yanmei Wen. Synthesis of Symmetrical (E,E)-1,4-Diaryl-1,3-butadienes by One-Pot Method [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2116-2120.
[5]	Peng Zhou, Shangwei Feng, Huihua Qiu, Jiantao Zhang. Sodiump-Toluenesulfinate/KI-Mediated Aerobic Oxidative Iodination of Terminal Alkynes for Synthesis of 1-Iodoalkynes and 1,3-Diynes [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 394-399.
[6]	Yao Ming, Zhang Jingjing, Yang Sen, Xiong Hangxing. γ-Aluminum Oxide-Mediated Iodination of Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2153-2158.
[7]	Hu Zhifang, Peng Lifen, Qiu Renhua, Orita Akihiro. Recent Progress of Protecting Groups for Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3112-3119.
[8]	Wang, Yaqi, Yin, Qiang, Guo, Dun, Han, Limin, Sun, Qi, Hong, Hailong, Suo, Quanling, Suo. Quanling. Carbonyl Cobalt-Catalyzed Cyclotrimerization of Terminal Alkynes in Supercritical Carbon Dioxide [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2898-2905.
[9]	Ma Nan, Zeng Xianghua. Cu₂O-Catalyzed Green Oxidative Terminal Alkynes Homocoupling without Bases [J]. Chin. J. Org. Chem., 2018, 38(6): 1556-1561.
[10]	Qi Haitang, Song Guanglin, Quan Zhengjun, Wang Xicun. CuSO₄·5H₂O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes [J]. Chin. J. Org. Chem., 2017, 37(7): 1855-1859.
[11]	Guan Zhipeng, Shi Yao, Shi Wei, Chen Hao. Synthesis of Terminal Alkynes/Diynes through Deprotection of Acetone Protected Alkynes under Mild Conditions [J]. Chin. J. Org. Chem., 2017, 37(2): 418-422.
[12]	Wang Chao, Deng Nan, Wang Lingling, Xu Dingjian, Yao Xiaoquan. Cu-Ag Bimetallic Nanoparticles Catalyzed Addition of Terminal Alkynes to Aldehydes [J]. Chin. J. Org. Chem., 2016, 36(5): 1034-1043.
[13]	Li Fuwei, Wang Xiaolong, Yu Haitao. Preparation of 1,3,5-Trisubstituted Pyrazoles with Cascade Reaction Catalyzed by Cu between Hydrazonoyl Halide and Terminal Alkynes [J]. Chin. J. Org. Chem., 2016, 36(5): 1127-1132.
[14]	Li Yibiao, Cheng Liang, Chen Lu, Li Bin, Sun Ning, Qing Ning. One-Pot Synthesis of Substituted Thiophene and Furan Derivatives from Terminal Alkynes [J]. Chin. J. Org. Chem., 2016, 36(10): 2426-2436.
[15]	Wu Gongde, Wang Xiaoli, Zhang Liming, Zhang Fang, Liu Xianfeng, Liu Congrong. One-Step Synthesis of 2,4-Disubstituted Thiazoles in Au(I) Complex/Zinc Salt Catalytic System [J]. Chin. J. Org. Chem., 2015, 35(12): 2537-2544.