Catalytic hydration of alkynes with Zeise's dimer

Hiscox, William C.; Jennings, P. W.

doi:10.1021/om00157a005

Cited by 144 publications

(55 citation statements)

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“…For instance, 1-heptyne is hydrated to 2-heptanone in 93 % yield. [171] 2-Hexyne forms 3-hexanone (65 %) and 2-hexanone (35 %); 4,4-dimethyl-3-pentanone (61-78 %) and 4,4-dimethyl-2-pentanone (24-39 % are formed from 4,4-dimethyl-2-pentyne. [172] Regioselective reactions take place when the platinum moiety is forced aside from the alkyne center by steric factors creating a partial cationic center at the distal carbon atom at which the water molecule attacks.…”

Section: Angewandte Chemiementioning

confidence: 99%

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

et al. 2004

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The regioselective functionalization of terminal alkenes and alkynes is of utmost importance for the synthesis of a wide variety of organic products. Based on the original observation by Vladimir Markovnikov-the pioneer of this field of research-in the 19th century, the possible regioisomeric products are classified as Markovnikov or anti-Markovnikov products. Contrary to traditional belief, it is nowadays possible to control the regiochemistry of various additions of nucleophiles to alkenes and alkynes by applying different transition-metal catalysts. Recent developments in this area of selective functionalization of alkenes and alkynes are reviewed.

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Section: Angewandte Chemiementioning

confidence: 99%

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

et al. 2004

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“…The catalytic activity observed for PtCl 2 under similar conditions and X-ray photoelectron spectroscopy (XPS) measurements of the final mixture confirms this reduction. Differently from previous work, [86,87] a s addition of water to Pt II is firmly suggested, to form the 18 e À complex 61. Intramolecular attack (62) followed by hydride transfer to Pt gives the Pt IV complex 63, which finally is reduced to 60 with the release of the product 52.…”

Section: Platinum Catalystsmentioning

confidence: 74%

“…[38,[86][87][88] Firstly, Jennings and coworkers used Zeises dimer 47 as a catalyst for the hydration of terminal and internal alkynes (Scheme 7). [86] The amount of catalyst needed was low (< 1 mol %) in boiling THF.…”

Section: Platinum Catalystsmentioning

confidence: 99%

Similarities and Differences between the “Relativistic” Triad Gold, Platinum, and Mercury in Catalysis

2011

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Relativistic effects in the valence shell of the elements reach a maximum in the triad Pt-Au-Hg and determine their catalytic activity in organic reactions. In this Review we examine the catalytic activity of Pt, Au, and Hg compounds for some representative reactions, and discuss the respective benefits and disadvantages along with other relevant properties, such as toxicity, price, and availability. For the reactions considered, gold catalysts are generally more active than mercury or platinum catalysts.

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“…5 Other metal-based catalysts which catalyze the Markovnikov as well as anti-Markovnikov hydration include NaAuCl 4 , RuCl 3 and [Ru(III)(EDTA-H)Cl], RhCl 3 , PtCl 4 and the Zeise dimer [{PtCl 3 (CH 2 =CH 2 )} 2 ], just to name a few. 6,7,8,9,10,11,12,13 Besides these homogenous catalysts also heterogenous catalyst systems are used. 14,15,16 The first ruthenium(II) complex to be known to catalyze the anti-Markovnikov hydration was a phosphine complex described by Tokunaga and Wakatsuki.…”

Section: Introductionmentioning

confidence: 99%

Ruthenium piano-stool complexes bearing imidazole-based PN ligands

Kunz

Thiel

Noffke

et al. 2012

Journal of Organometallic Chemistry

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A variety of piano-stool complexes of cyclopentadienyl ruthenium(II) with imidazole-based PN ligands have been synthesized starting from the precursor complexes CpRu(C10H8)]PF6, CpRu(NCMe)(3)]PF6 and CpRu(PPh3)(2)Cl]. PN ligands used are imidazol-2-yl, -4-yl and -5-yl phosphines. Depending on the ligand and precursor different types of coordination modes were observed; in the case of polyimidazolyl PN ligands these were kappa P-1-monodentate, kappa P-2,N-, kappa N-2,N-and kappa N-3,N,N-chelating and mu-kappa P:kappa N-2,N-brigding. The solid-state structures of CpRu(1a)(2)Cl]center dot H2O (5 center dot H2O) and CpRu(mu-kappa(2)-N,N-kappa('1)-P-2b)(2)](C6H5PO3H)(2)(C6H5PO3H2)( 2), a hydrolysis product of the as well determined CpRu(2b) (2)](PF6)(2)center dot 2CH(3)CN (7b center dot 2CH(3)CN) were determined (1a = imidazol-2-yldiphenyl phosphine, 2b = bis(1-methylimidazol-2-yl) phenyl phosphine, 3a = tris(imidazol-2-yl) phosphine). Furthermore, the complexes CpRu(L) (2) [e] Anorganisch-Chemisches Institut, Universität Zürich-Irchel, Winterthurerstr. 190, CH-8057 Zürich, Switzerland.[ ‡] X-ray structure analysis.

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Catalytic hydration of alkynes with Zeise's dimer

Cited by 144 publications

References 1 publication

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

Catalytic Markovnikov and anti‐Markovnikov Functionalization of Alkenes and Alkynes: Recent Developments and Trends

Similarities and Differences between the “Relativistic” Triad Gold, Platinum, and Mercury in Catalysis

Ruthenium piano-stool complexes bearing imidazole-based PN ligands

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