Iron-catalyzed indirect hydration of alkynes in presence of methanesulfonic acid

Park, Jungmin; Yeon, Jihee; Lee, Phil Ho; Lee, Kooyeon

doi:10.1016/j.tetlet.2013.06.015

Cited by 71 publications

(42 citation statements)

References 37 publications

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“…851 Methanesulfonic acid was added to the alkyne in a regioselective manner, forming vinyl mesylates which underwent in situ hydrolysis to ketones. The utility of the method could be demonstrated using numerous alkynes including those bearing substituents such as halide, amide, and hydroxy at the benzene ring.…”

Section: Càheteroatom Bond Forming Additions To Càc Double and Triplementioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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Section: Càheteroatom Bond Forming Additions To Càc Double and Triplementioning

confidence: 99%

Iron Catalysis in Organic Synthesis

2015

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“…[18] This strategy was utilized as ak ey step in the synthesis of haloperidol and its derivatives. Te rminala lkylated phenylacetylene (12), acetophenone (13), and the vinyl ester (14) were tested and eliminated from consideration as the reaction intermediates [Eq. [19] This strategy therefore can be applied to the synthesis of pharmaceuticals and bioactive natural products in astep-economic way.…”

mentioning

confidence: 99%

Iron‐Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides

Zhu

et al. 2017

Chemistry A European J

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An iron-catalyzed oxyalkylation of alkynes with alkyl peroxides as the alkylating reagents has been investigated. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as the alkylating reagents and internal oxidants. Primary, secondary, and tertiary alkyl groups of aliphatic acids were readily incorporated into C-C triple bonds and diverse α-alkylated ketones were synthesized. Mechanism studies revealed that this reaction involves highly reactive alkyl free radicals. A unique equilibrium between lauric acid and water catalyzed by the iron(III) catalyst was observed.

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“…[38] To be second means being the last." [40]). [39] TheG old Medal for discovery of catalytic hydration of acetylenic hydrocarbons undoubtedly belongs to the famous Russian chemist Mikhail Kucherov. Unfortunately,h andbooks on chemistry or scientific articles do not always mention Kucherovsn ame when the hydration of alkynes is discussed.…”

Section: Scientific Olympusmentioning

confidence: 99%

Mikhail Kucherov: “The Experiment Confirmed my Hypothesis”

Rulev

Ponomarev

2019

Angew Chem Int Ed

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Named reactions are key points in the development of chemistry.A ny competent chemist easily identifies the reaction named after Wittig, or Grignard, Diels-Alder,o r Friedel-Crafts,Michael,orFavorsky.But how muchdowecan say about scientist who discovered it?This Essay is devoted to the transition-metal-catalyzed hydration of acetylenic hydrocarbons discovered by Russian chemist Mikhail Kucherov. This reaction is one of the most straightforwardm ethods for the synthesis of carbonyl compounds.W ith it, in industry for al ong time acetaldehyde was essentially manufactured from accessible unsaturated raw material-acetylene.T his reaction is one of the first steps in the establishment of homogenous metal complex catalysis in organic synthesis.H erein, we described the history of this discovery and the role of many scientists in the development of research in this field. We would also like to showthe life of Russian scientists in the latter half of the 19th century.

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Iron-catalyzed indirect hydration of alkynes in presence of methanesulfonic acid

Cited by 71 publications

References 37 publications

Iron Catalysis in Organic Synthesis

Iron Catalysis in Organic Synthesis

Iron‐Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides

Mikhail Kucherov: “The Experiment Confirmed my Hypothesis”

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