Journal ArticleDOI
Aqueous Baylis–Hillman reactions of cyclopent-2-enone using imidazole as catalyst
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TLDR
In aqueous media, imidazole was found to catalyse Baylis-Hillman reactions of cyclopent-2-enone with various aldehydes to afford the desired adducts with high yields as mentioned in this paper.About:
This article is published in Tetrahedron Letters.The article was published on 2002-10-07. It has received 73 citations till now. The article focuses on the topics: Enone & Imidazole.read more
Citations
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Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update
TL;DR: Reaction of R,â-Unsaturated Carbonyl Compounds 3127: Reaction of R-UnSaturated Carbonies 3127 7.1.6.
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Recent Advances in the Baylis−Hillman Reaction and Applications
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A Case Study of the Mechanism of Alcohol-Mediated Morita Baylis–Hillman Reactions. The Importance of Experimental Observations
TL;DR: A combination of mechanistic probes is used to define the mechanism and an experimental mechanistic free-energy profile for a prototypical Morita Baylis–Hillman reaction in methanol, and the ability of computations to predict the mechanism is critically evaluated.
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Remarkable Rate Acceleration of Imidazole-Promoted Baylis−Hillman Reaction Involving Cyclic Enones in Basic Water Solution
TL;DR: Bicarbonate solution was shown to be the optimal reaction medium for the Baylis-Hillman reaction with imidazoles as catalysts, which resulted in short reaction time, high yields, and expanding substrate scopes.
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Ionic Liquid-Immobilized Quinuclidine-Catalyzed Morita−Baylis−Hillman Reactions
TL;DR: The IL-supported catalyst showed equally good catalytic activity as compared with its nonimmobilized counterpart and can be readily recovered and reused six times without significant loss of catalyticActivity.
References
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Journal ArticleDOI
Efficient Baylis--Hillman reaction using stoichiometric base catalyst and an aqueous medium.
Chengzhi Yu,Bin Liu,Longqin Hu +2 more
TL;DR: Deuterium-exchange experiments suggest that the Michael addition adduct formed between DABCO and methyl acrylate is the active intermediate for the Baylis--Hillman reaction in aqueous conditions, and its hydrolysis, a nonproductive side reaction facilitated by the quaternary ammonium ion.
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Efficient Baylis–Hillman reactions promoted by mild cooperative catalysts and their application to catalytic asymmetric synthesis
TL;DR: In this article, mild cooperative catalysts of tributylphosphine with phenols such as (±)-1,1′-bi-2-naphthol (BINOL) were used to give α-methylene-β-hydroxyalkanones in high yield.
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DMAP-catalyzed hydroxymethylation of 2-cyclohexenones in aqueous medium through Baylis-Hillman reaction
TL;DR: In this paper, the reaction of 2-cyclohexenones 1a-d with aqueous formaldehyde, catalyzed by DMAP in THF, affords the corresponding 2-(hydroxymethyl)-2-cycloenones 2a-D in good yields.
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Lewis base and L-proline co-catalyzed Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone
TL;DR: In this article, the Baylis-Hillman reaction of arylaldehydes with methyl vinyl ketone was investigated in the presence of a catalytic amount of l -proline, weak bases such as imidazole and triethylamine as well as the stronger Lewis base DABCO.
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Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes.
Chengzhi Yu,Longqin Hu +1 more
TL;DR: This represents the first demonstration of the Baylis-Hillman reaction of aldehydes with acrylamides, which were thought to be inert under atmospheric pressure and at ambient temperature.
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Efficient Baylis--Hillman reaction using stoichiometric base catalyst and an aqueous medium.
Chengzhi Yu,Bin Liu,Longqin Hu +2 more