NC palladacycles in the Heck arylation of ethylene: Synthesis, structure and their reactivity

Atla, Shashi B.; Kelkar, Ashutosh A.; Puranik, Vedavati G.; Bensch, Wolfgang; Chaudhari, Raghunath V.

doi:10.1016/j.jorganchem.2008.11.065

Cited by 29 publications

(23 citation statements)

References 35 publications

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“…Organometallic palladium complexes containing cyclometalated ligands have attracted widespread interest for applications as anti-cancer treatments [1][2][3][4][5] and in catalysis [6][7][8][9][10][11], together with their novel physical properties [12][13][14][15][16][17] [13,22].…”

Section: Introductionmentioning

confidence: 99%

“…Found: C, 49.4, H, 3.6, N, 8.2 % IR(KBr) 3211-3168s, 2923w, 1683vs, 1602s, 1581m 405m cm -1 . 1H NMR (dmso-d6 ), δ 9.74 (s, 1H, NH), 9.35 (d, 1H, J 3.9), 8.65 (d, 1H, J 7.9), 7.84 (ddd, 1H, J 7.9), 7.79 (d, 1H, J 7.9), 7.67 (d, 1H, J 7.9), 7.43 (d, 1H, J 7.9), 7.28 (ddd, 1H, J 7.9), 7.19 (ddd, 1H, J 5.9), 7.08 (ddd, 9 1H, J 7.9), 6.89 (ddd, 1H, J 7.9),6.10 (d, 1H, J 7.9), 2.38 (s, 3H, MeCO), 2.23 (s, 3H, Me). Mp 310 C decomposes.…”

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confidence: 99%

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Synthesis and molecular structures of palladium(II) metalated 2-phenylpyridine complexes [PdCl(pyC6H4)L] containing amino- or acetylamino-pyridine co-ligands

Al‐Jibori

Gergees

Al-Rubaye

et al. 2016

Inorganica Chimica Acta

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Section: Introductionmentioning

confidence: 99%

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confidence: 99%

Synthesis and molecular structures of palladium(II) metalated 2-phenylpyridine complexes [PdCl(pyC6H4)L] containing amino- or acetylamino-pyridine co-ligands

Al‐Jibori

Gergees

Al-Rubaye

et al. 2016

Inorganica Chimica Acta

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“…[14b] Because of their superior thermal stability relative to the Pd(OAc) 2 /PAr 3 system, such complexes were intended for palladium(0)-catalyzed reactions which require temperatures of 140 °C or greater. [15] However, ethylene arylation products undergo polymerization at this temperature.…”

Section: Mizoroki–heck-type Reactions Of Ethylenementioning

confidence: 99%

“…The following year, RajanBabu and co-workers reported a similar reaction with broader substrate scope. [14a] …”

Section: Mizoroki–heck-type Reactions Of Ethylenementioning

confidence: 99%

Transition‐Metal‐Catalyzed Laboratory‐Scale Carbon–Carbon Bond‐Forming Reactions of Ethylene

2013

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Ethylene, the simplest alkene, is the most abundantly synthesized organic molecule by volume. It is readily incorporated into transitionmetal–catalyzed carbon-carbon bond-forming reactions through migratory insertions into alkylmetal intermediates. Because of its D2h symmetry, only one insertion outcome is possible. This limits byproduct formation and greatly simplifies analysis. As described within this Minireview, many carbon–carbon bond-forming reactions incorporate a molecule (or more) of ethylene at ambient pressure and temperature. In many cases, a useful substituted alkene is incorporated into the product.

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“…Heck cross-coupling is an important method for carbon–carbon bond synthesis, and has greatly attracted more and more attention for its wide application in the synthesis of dyes, medicines, natural products, pesticides, perfumes, cinnamic acid derivatives, and new polymer materials [ 1 , 2 , 3 , 4 , 5 ]. The palladium-catalyzed Mizoroki–Heck cross-coupling reaction represents one of the most valuable methods for carbon–carbon bond formation in organic synthesis [ 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

O-Carboxymethyl Chitosan Supported Heterogeneous Palladium and Ni Catalysts for Heck Reaction

Zhang

2017

Molecules

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Two polymer catalysts (Pd-OCMCS and Ni-OCMCS) with good reusability were synthesized by coordinating Pd and Ni onto O-carboxymethyl chitosan (OCMCS). The chemical structure and thermal stability of prepared catalysts were determined by Fourier transform infrared (FT-IR) spectra, Energy Dispersive Spectrometer (EDS)analysis, X-ray diffraction (XRD), and thermogravimetric analyzer (TG-DTG), and the analysis results showed that the Pd and Ni ions coordinated onto the OCMCS and formed a ligand with the –COOH group, amino groups, and –OH group on the OCMCS, and the EDS and Inductively Coupled Plasma Optical Emission Spectrometry (ICP-OES) analysis results showed that the loading amounts of Pd and Ni were approximately 8.3% and 8.9%, respectively. In the Heck reaction between aryl halides and n-butyl acrylate catalyzed by the prepared catalyst, the test results showed that the product yield followed the order of aryl iodide > aryl bromide > aryl chloride. Additionally, the product yield for the aryl iodide and aryl bromide could reach up to 99% and 96%, respectively. Moreover, the electron-withdrawing and electron-donating property of the group on the aryl also affected the product yield, and the product yield for aryl halides with electron-withdrawing group p-NO2, p-CH3CO, and p-CHO was higher than that with electron-donating group p-CH3.

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NC palladacycles in the Heck arylation of ethylene: Synthesis, structure and their reactivity

Cited by 29 publications

References 35 publications

Synthesis and molecular structures of palladium(II) metalated 2-phenylpyridine complexes [PdCl(pyC6H4)L] containing amino- or acetylamino-pyridine co-ligands

Synthesis and molecular structures of palladium(II) metalated 2-phenylpyridine complexes [PdCl(pyC6H4)L] containing amino- or acetylamino-pyridine co-ligands

Transition‐Metal‐Catalyzed Laboratory‐Scale Carbon–Carbon Bond‐Forming Reactions of Ethylene

O-Carboxymethyl Chitosan Supported Heterogeneous Palladium and Ni Catalysts for Heck Reaction

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