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Issue 4, 2015
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Task-specific ionic liquid and CO2-cocatalysed efficient hydration of propargylic alcohols to α-hydroxy ketones

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Abstract

The hydration of propargylic alcohols is a green route to synthesize α-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 α-hydroxy ketones in good to excellent yields. In the IL/CO2 reaction system, CO2 served as a cocatalyst by forming α-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.

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

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Publication details

The article was received on 06 Jan 2015, accepted on 15 Jan 2015 and first published on 15 Jan 2015


Article type: Edge Article
DOI: 10.1039/C5SC00040H
Chem. Sci., 2015,6, 2297-2301
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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

    Y. Zhao, Z. Yang, B. Yu, H. Zhang, H. Xu, L. Hao, B. Han and Z. Liu, Chem. Sci., 2015, 6, 2297
    DOI: 10.1039/C5SC00040H

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