A ruthenium-catalyzed one-pot method for α-alkylation of ketones with aldehydes

Cho, Chan Sik; Shim, Sang Chul

doi:10.1016/j.jorganchem.2006.07.005

Cited by 36 publications

(17 citation statements)

References 26 publications

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“…A further improvement of the reaction was observed by introducing the catalyst [RuCl 2 (PPh 3 ) 3 ] 9. However, in this case the use of a hydrogen acceptor (1‐dodecene) was compulsory to prevent the over‐reduction of the final alkylated ketone to the corresponding alcohol of type 8 (see Scheme 2; 1,4‐dioxane was the source of the extra hydrogen for this final over‐reduction10). With this ruthenium complex, not only alkyl aryl ketones but also dialkyl ketones could be successfully alkylated (Table 1, entry 2).…”

Section: Electrophilic α‐Alkylation Of Ketonesmentioning

confidence: 99%

Alcohols as Electrophiles in CC Bond‐Forming Reactions: The Hydrogen Autotransfer Process

2007

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The hydrogen autotransfer process involves an initial oxidative hydrogen elimination, followed by different types of reactions, and is completed with a reductive hydrogen addition to give the final product. The sequence allows the alkylation of different nucleophilic agents using environmentally benign alcohols as electrophiles, mild conditions, and soft bases, with water produced as the only waste material. Recent examples of modulating the organometallic catalyst have also lent themselves to expansion of the range of available substrates, as described in this Minireview.

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Section: Electrophilic α‐Alkylation Of Ketonesmentioning

confidence: 99%

Alcohols as Electrophiles in CC Bond‐Forming Reactions: The Hydrogen Autotransfer Process

2007

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“…A similar catalytic cycle has been proposed by us in ruthenium-catalyzed cross-coupling reactions. [6,8,9] wileyonlinelibrary.com/journal/aoc …”

Section: Resultsmentioning

confidence: 99%

“…[8] In addition, it was also demonstrated that ketones 1 were found to be coupled with aldehydes 6 to give coupled ketones 3 (Scheme 1, route d). [9] Several other transition metal precursors have also been introduced for such sp 3 -carbon-sp 3 -carbon bond-forming reactions, [10 -16] and this coupling protocol could be applied to modified Friedländer quinoline synthesis. [17 -26] Prompted by these findings, this report describes another ruthenium-catalyzed one-pot multicatalytic coupling mode between secondary alcohols 5 and aldehydes 6, leading to coupled ketones 3 or coupled secondary alcohols 4 by the tuning of the molar ratio of [5]: [6] and the presence (or absence) of a hydrogen acceptor (Scheme 1, routes e and f).…”

Section: Introductionmentioning

confidence: 99%

Carbon–carbon bond formation between secondary alcohols and aldehydes under ruthenium‐catalyzed redox shuttle

Cho

Kim

Yoon

2011

Applied Organom Chemis

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“…By chemical means, dihydrochalcones are obtained by regioselective reduction of carbon-carbon double bond in α,β-unsaturated ketones. One of the methods uses gaseous hydrogen, of which addition to the double bond is catalysed by ruthenium salts in dioxane at 80 • C [52].…”

Section: Chemical Synthesis Of Dihydrochalconesmentioning

confidence: 99%

Dihydrochalcones: Methods of Acquisition and Pharmacological Properties—A First Systematic Review

2019

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Dihydrochalcones are a class of secondary metabolites, for which demand in biological and pharmacological applications is still growing. They posses several health-endorsing properties and, therefore, are promising candidates for further research and development. However, low content of dihydrochalcones in plants along with their low solubility and bioavailability restrict the development of these compounds as clinical therapeutics. Therefore, chemomicrobial and enzymatic modifications are required to expand their application. This review aims at analyzing and summarizing the methods of obtaining dihydrochalcones and of presenting their pharmacological actions that have been described in the literature to support potential future development of this group of compounds as novel therapeutic drugs. We have also performed an evaluation of the available literature on beneficial effects of dihydrochalcones with potent antioxidant activity and multifactorial pharmacological effects, including antidiabetic, antitumor, lipometabolism regulating, antioxidant, anti-inflammatory, antibacterial, antiviral, and immunomodulatory ones. In addition, we provide useful information on their properties, sources, and usefulness in medicinal chemistry.

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A ruthenium-catalyzed one-pot method for α-alkylation of ketones with aldehydes

Cited by 36 publications

References 26 publications

Alcohols as Electrophiles in CC Bond‐Forming Reactions: The Hydrogen Autotransfer Process

Alcohols as Electrophiles in CC Bond‐Forming Reactions: The Hydrogen Autotransfer Process

Carbon–carbon bond formation between secondary alcohols and aldehydes under ruthenium‐catalyzed redox shuttle

Dihydrochalcones: Methods of Acquisition and Pharmacological Properties—A First Systematic Review

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