Task-specific ionic liquid and CO2-cocatalysed efficient hydration of propargylic alcohols to α-hydroxy ketones

被引:95
作者
Zhao, Yanfei [1 ]
Yang, Zhenzhen [1 ]
Yu, Bo [1 ]
Zhang, Hongye [1 ]
Xu, Huanjun [1 ]
Hao, Leiduan [1 ]
Han, Buxing [1 ]
Liu, Zhimin [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Key Lab Colloid Interface & Thermodynam, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYZED HYDRATION; ROOM-TEMPERATURE; ALKYNES; NANOPARTICLES;
D O I
10.1039/c5sc00040h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The hydration of propargylic alcohols is a green route to synthesize alpha-hydroxy ketones. Herein a CO2-reactive ionic liquid (IL), [Bu4P][Im], was found to display high performance for catalyzing the hydration of propargylic alcohols in the presence of atmospheric CO2, and a series of propargylic alcohols could be converted into the corresponding alpha-hydroxy ketones in good to excellent yields. In the IL/CO2 reaction system, CO2 served as a cocatalyst by forming alpha-alkylidene cyclic carbonates with propargylic alcohols, and was released via the rapid hydrolysis of the carbonates catalysed by the IL. This is the first example of the efficient hydration of propargylic alcohols under metal-free conditions.
引用
收藏
页码:2297 / 2301
页数:5
相关论文
共 39 条
[1]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[2]   Ionic liquids for the convenient synthesis of functional nanoparticles and other inorganic nanostructures [J].
Antonietti, M ;
Kuang, DB ;
Smarsly, B ;
Yong, Z .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (38) :4988-4992
[3]   Catalyzed reactions of alkynes in water [J].
Chen, Liang ;
Li, Chao-Jun .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1459-1484
[4]   Self-assembled bidentate ligands for Ru-catalyzed anti-Markovnikov hydration of terminal alkynes [J].
Chevallier, F ;
Breit, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (10) :1599-1602
[5]   Tuning Anion-Functionalized Ionic Liquids for Improved SO2 Capture [J].
Cui, Guokai ;
Zheng, Junjie ;
Luo, Xiaoyan ;
Lin, Wenjun ;
Ding, Fang ;
Li, Haoran ;
Wang, Congmin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (40) :10620-10624
[6]   AgOTf catalyzed hydration of terminal alkynes [J].
Das, Rima ;
Chakraborty, Debashis .
APPLIED ORGANOMETALLIC CHEMISTRY, 2012, 26 (12) :722-726
[7]   Efficient synthesis of tertiary α-hydroxy ketones through CO2-promoted regioselective hydration of propargylic alcohols [J].
He, Haitao ;
Qi, Chaorong ;
Hu, Xiaohan ;
Guan, Yuqi ;
Jiang, Huanfeng .
GREEN CHEMISTRY, 2014, 16 (08) :3729-3733
[8]   Catalytic hydration of Alkynes and its application in synthesis [J].
Hintermann, Lukas ;
Labonne, Aurelie .
SYNTHESIS-STUTTGART, 2007, (08) :1121-1150
[9]   The selective addition of water to C=C bonds; enzymes are the best chemists [J].
Jin, Jianfeng ;
Hanefeld, Ulf .
CHEMICAL COMMUNICATIONS, 2011, 47 (09) :2502-2510
[10]   Heterogeneously Catalyzed Efficient Hydration of Alkynes to Ketones by Tin-Tungsten Mixed Oxides [J].
Jin, Xiongjie ;
Oishi, Takamichi ;
Yamaguchi, Kazuya ;
Mizuno, Noritaka .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (04) :1261-1267