Cerium(IV) Sulfate-Catalyzed Hydration of Alkynes

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Chin. J. Org. Chem. ›› 2006, Vol. 26 ›› Issue (08): 1073-1078. Previous Articles Next Articles

Original Articles

硫酸高铈催化炔烃的水合反应研究

刘文杰¹,2，李金恒*^,1

(¹湖南师范大学化学化工学院长沙 410081)
(²新疆塔里木大学文理学院阿拉尔 843300)

收稿日期:2005-10-18 修回日期:2006-02-10 发布日期:2006-07-26
通讯作者: 李金恒

Cerium(IV) Sulfate-Catalyzed Hydration of Alkynes

LIU Wen-Jie¹,2,LI Jin-Heng*^,1

(¹ College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081)
(² Arts and Science College, Tarim University, Ala 843300)

Received:2005-10-18 Revised:2006-02-10 Published:2006-07-26

Contact: LI Jin-Heng

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Abstract

An inexpensive and highly selective method for cerium(IV) sulfate-catalyzed hydration of alkynes was provided. Treatment of alkynes (1 mmol) with Ce(SO₄)₂ (0.1 mmol), H₂SO₄ (conc. 0.06 mL), water (0.02 mL) and benzene (5 mL) at 70 ℃ afforded the corresponding ketones in moderate to excellent yields.

Key words: hydration reaction, cerium(IV) sulfate, ketone, alkyne

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LIU Wen-Jie^1,2,LI Jin-Heng*^,1. Cerium(IV) Sulfate-Catalyzed Hydration of Alkynes[J]. Chin. J. Org. Chem., 2006, 26(08): 1073-1078.

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[1]	Wenwen Chen, Qin Zhang, Songyue Zhang, Fangfang Huang, Xinyin Zhang, Jianfeng Jia. Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 584-592.
[2]	Wenfeng Bei, Jian Pan, Dongmei Ran, Yilin Liu, Zhen Yang, Ruokun Feng. Cobalt-Catalyzed [4+2] Annulation of Indole Carboxamide with Diynes and Monoacetylene: Direct Access to γ-Carbolinones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3226-3238.
[3]	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.
[4]	Wenqian Wu, Chunxia Chen, Jinsong Peng, Zhanyu Li. Research Progress of Carbonyl α-Position Amination [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2743-2763.
[5]	Suzhen Zhang, Wenwen Zhang, Hui Yang, Qing Gu, Shuli You. Rhodium-Catalyzed Enantioselective Spiroannulation of 2-Alkenylphenols with Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2926-2933.
[6]	Kai Lu, Haoqi Qu, Xi Chen, Hui Qiu, Jing Zheng, Mengtao Ma. Catalyst-Free and Solvent-Free Hydroboration of Alkynes and Alkenes with Catecholborane [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2197-2205.
[7]	Jiamin Ma, Jiaoxiong Li, Qiansen Meng, Xianghua Zeng. Advances on the Radical Sulfonation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2040-2052.
[8]	Zhihao Chen, Qi Fan, Biaolin Yin, Qingjiang Li, Honggen Wang. Progress in the Syntheses of α-Boryl Carbonyl Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1706-1712.
[9]	Sida Li, Xing-Zhong Shu, Lipeng Wu. Zirconium and Titanium Mediated Hydroboration of Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1751-1760.
[10]	Shiquan Gao, Chuangjun Liu, Junfeng Yang, Junliang Zhang. Cobalt-Catalyzed Electrochemical Reductive Coupling of Alkynes and Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1559-1565.
[11]	Peng Liu, Fuming Zhong, Lihao Liao, Weiqiang Tan, Xiaodan Zhao. Progress in the Construction of Spirocyclohexadienones via Alkyne-Involving Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4019-4035.
[12]	Peng Zhou, Weiming Zhu, Jiantao Zhang, Duoduo Xiao, Xiangfeng Guo, Weibing Liu. Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3939-3944.
[13]	Yuehua Zhang, Fei Nie, Lu Zhou, Xiaofeng Wang, Yuan Liu, Yanping Huo, Wencheng Chen, Zujin Zhao. Synthesis and Optoelectronic Studies of Thermally Activated Delayed Fluorescence Materials Based on Benzothiazolyl Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3876-3887.
[14]	Duoduo Xiao, Jiantao Zhang, Peng Zhou, Weibing Liu. Metal-Free α-C(sp³)—H Methylenation of Aryl Ketones to Form γ-Keto Sulfoxides with Dimethyl Sulfoxide [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3900-3906.
[15]	Yunpeng Qi, Dengkai Lin, Liang-An Chen. Research Progress on Reductive Acylation with Acyl-Ni as a Key Intermediate to Synthesize Ketones [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3861-3875.