Catalytic Hydration Of Alkynes Research Articles

Indazolin-s-ylidene–N-Heterocyclic Carbene Complexes of Rhodium, Palladium, and Gold: Synthesis, Characterization, and Catalytic Hydration of Alkynes

A novel series of Indy-N-heterocyclic carbene ligands (Indy = indazolin- s-ylidene) have been developed and investigated. Via a mild Ag carbene transfer route, these new carbene ligands reacted with rhodium, palladium, and gold salts to yield the corresponding air-stable metal complexes. The product complexes were characterized by NMR spectroscopic methods and X-ray diffraction analysis. The electronic properties of these complexes were modified by the introduction of different substituents at the coordinated NHC ligands. Catalytic properties of the gold complex were evaluated in the hydration of alkynes to give the corresponding ketone products. This new type of gold N-heterocyclic carbene complex showed a high catalytic activity in the hydration of alkyne at room temperature.

Catalytic Hydration of Alkynes over Brønsted Acid Sites Developed on Halide Clusters

When a molecular tungsten halide cluster on silica gel, (H3O)2[(W6Cl8)Cl6] · 6H2O/SiO2, was treated in a nitrogen stream at temperatures above 250 °C, Bronsted acidity appeared as the result of formation of a hydroxo ligand. The cluster catalyzed hydration of 1-hexyne to yield 2-hexanone. The catalytic activity increased with increasing temperature, the selectivity for 2-hexanone being 70% in the temperature range 250–400 °C. 1-Heptyne, 1-octyne, 1-nonyne, and phenylacetylene were also preferentially hydrated to produce the corresponding ketones. 2-Hexyne provided 2- and 3-hexanones in equal amounts, as happens with Bronsted acid catalysts. Halide clusters of niobium, molybdenum, and tantalum having the same octahedral metal framework were also active catalysts for the reaction.

Catalytic Hydration of Alkynes and Its Application in Synthesis

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Catalytic Hydration of Alkynes and Its Application in Synthesis

The catalytic addition of water to alkynes (hydration) generates valuable carbonyl compounds from unsaturated hydrocarbon precursors. Traditional mercury(II) catalysts hydrate terminal alkynes with Markovnikov selectivity to methyl ketones. Much research has been devoted to finding catalysts based on less toxic metals, the most promising being gold(I), gold(III), platinum(II), and palladium(II). Catalytic anti-Markovnikov hydration of terminal alkynes to aldehydes has been realized in an efficient manner with ruthenium(II) complex catalysts. The present review article lists known hydration catalysts and discusses applications of catalytic hydration to different classes of substrates, with an emphasis on functional group tolerance and regioselectivity.

Insight into the Selective Room-Temperature Platinum(II) Catalytic Hydration of Alkynes in Water

Three platinum complexes of water-soluble, bidentate phosphine ligands have been prepared and characterized. The complexes, PtCl2(P−P) (P−P = (m-NaSO3C6H4)2PCH2CH2P(m-C6H4SO3Na)2, DPPETS, (m-NaSO3C6H4)2PCH2CH2CH2P(m-C6H4SO3Na)2, DPPPTS, (m-NaSO3C6H4)2PCH2CH2CH2CH2P(m-C6H4SO3Na)2, DPPBTS), catalyze the hydration of 3-pentyn-1-ol and 4-pentyn-1-ol. 2-Pentyn-1-ol is slowly polymerized, allowing characterization of the intermediate η1-allenyl complexes. For PtCl2(DPPBTS) the η1-allenyl complex Pt(C(Et)CCH2)(X)(DPPBTS), where X is either OH-, OH2, or Cl-, is formed. However for PtCl2(DPPPTS) and PtCl2(DPPETS) the extent of formation of the coordinated complex is much less. The stability of the coordinated Pt(η1-allenyl)(X)(P−P) complexes shows a significant effect on chelate ring size, with DPPBTS > DPPPTS > DPPETS being the order of decreasing stability. Catalytic hydrations of 4-pentyn-1-ol with PtCl2(P−P) show a major effect of chelate ring size in the opposite direction, DPPETS > DPPPTS > DPPBTS. For 3-pen...

Catalytic hydration of alkynes with platinum(II) complexes

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCatalytic hydration of alkynes with platinum(II) complexesJ. W. Hartman, W. C. Hiscox, and P. W. JenningsCite this: J. Org. Chem. 1993, 58, 26, 7613–7614Publication Date (Print):December 1, 1993Publication History Published online1 May 2002Published inissue 1 December 1993https://doi.org/10.1021/jo00078a056RIGHTS & PERMISSIONSArticle Views737Altmetric-Citations92LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (192 KB) Get e-Alerts Get e-Alerts

Catalytic hydration of alkynes with Zeise's dimer

Pt(II) in the form of Zeise's dimer has been shown to be an efficient and facile hydration catalyst or catalyst precursor for the hydration of alkyl-substituted alkynes.