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

Yanfei Zhao; Zhenzhen Yang; Bo Yu; Hongye Zhang; Huanjun Xu; Leiduan Hao; Buxing Han; Zhimin Liu

doi:10.1039/c5sc00040h

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

Yanfei Zhao, Zhenzhen Yang, Bo Yu, Hongye Zhang, Huanjun Xu, Leiduan Hao, Buxing Han, Zhimin Liu

Research output: Contribution to journal › Article › peer-review

93 Scopus citations

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.

Original language	English
Pages (from-to)	2297-2301
Number of pages	5
Journal	Chemical Science
Volume	6
Issue number	4
DOIs	https://doi.org/10.1039/c5sc00040h
State	Published - Apr 1 2015
Externally published	Yes

Funding

Funders	Funder number
National Natural Science Foundation of China	21321063, 21125314, 21403252

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

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.",

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AU - Zhao, Yanfei

AU - Yang, Zhenzhen

AU - Yu, Bo

AU - Zhang, Hongye

AU - Xu, Huanjun

AU - Hao, Leiduan

AU - Han, Buxing

AU - Liu, Zhimin

PY - 2015/4/1

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AB - 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.

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

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