Oxometallate-Based Ionic Liquid Catalyzed CO2-Promoted Hydration of Propargylic Alcohols for α-Hydroxy Ketones
Yuankun Wang1,2, Chongli Wang1,2, Weidong Lin1,2
1State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, China.
Abstract:
α-Hydroxy ketones are a crucial class of organic compounds prevalent in natural products and pharmaceutical molecules. The CO2-promoted hydration of propargylic alcohols is an efficient method for the synthesis of α-hydroxy ketones. Herein, an ionic liquid (IL) was designed to catalyze this reaction individually under atmospheric CO2 pressure, volatile organic solvents, and additives. This IL, constructed from the molybdate anion, can be recycled from industrial (NH4)2MoO4 production wastewater, demonstrating its high tolerance to catalytic environments and significant potential for practical applications. To our knowledge, this is the first instance of an oxometallate-based IL catalyst being utilized for the CO2-promoted hydration of propargylic alcohols. Further mechanistic studies revealed the bifunctionality of this IL in activating both CO2 and substrates.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
07:36Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Related Concept Videos
02:45Acid-Catalyzed Hydration of Alkenes
01:20Aldehydes and Ketones with Water: Hydrate Formation
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
02:40Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
02:15Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
02:35Acid-Catalyzed Dehydration of Alcohols to Alkenes
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration