An efficient trifunctional benzhydrazone ligated Pd(II) complex for Heck reaction of aryl bromides

Muthumari, Subramanian; Mohan, Nanjan; Ramesh, Rengan

doi:10.1016/j.tetlet.2015.05.016

Cited by 24 publications

(5 citation statements)

References 50 publications

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“…There is essentially no deviation (0.002(1)–0.005(3) Å) of the metal centre from the plane (rmsd 0.008–0.035 Å) constituted by the four coordinating atoms. In general, the metal to coordinating atom bond lengths are unexceptional and comparable with the corresponding bond lengths observed in mononuclear palladium(II) complexes containing similar coordinating atoms …”

Section: Resultssupporting

confidence: 59%

Triphenylphosphinopalladium(II) complexes with ONO‐donor ligands: syntheses, structures and catalytic applications in CC cross‐coupling reactions

Prabhu

Babu

Pal

2016

Applied Organom Chemis

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Reactions of 1-((2-hydroxy-5-R-phenylimino)methyl)naphthalen-2-ols (H 2 L n , n = 1-3 for R = H, Me, Cl, respectively) with [Pd(PPh 3 ) 2 Cl 2 ] and Et 3 N in toluene under reflux produced three new mononuclear square-planar palladium(II) complexes with the general formula [Pd(L n )(PPh 3 )] (1, R = H; 2, R = Me; 3, R = Cl). All the complexes were characterized using elemental analysis, solution conductivity and various spectroscopic (infrared, UV-visible and NMR) measurements. Molecular structures of 1-3 were confirmed using single-crystal X-ray diffraction analysis. In each complex, the fused 5,6-membered chelate rings forming phenolate-O, azomethine-N and naphtholate-O donor (L n ) 2À and the PPh 3 form a square-planar ONOP coordination environment around the metal centre. Infrared and NMR spectroscopic features of 1-3 are consistent with their molecular structures. Electronic spectra of the three complexes display several strong primarily ligand-centred absorption bands in the range 322-476 nm. All the complexes were found to be effective catalysts for carbon-carbon cross-coupling reactions of arylboronic acids with aromatic and heteroaromatic aldehydes to form the corresponding diaryl ketones.

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Section: Resultssupporting

confidence: 59%

Triphenylphosphinopalladium(II) complexes with ONO‐donor ligands: syntheses, structures and catalytic applications in CC cross‐coupling reactions

Prabhu

Babu

Pal

2016

Applied Organom Chemis

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“…Benzhydrazone ligands were developed by the reaction of 4-(diethylamino)-2-hydroxybenzaldehyde with benzhydrazide derivatives in a 1 : 1 ratio in ethanol medium as reported in the literature. 19 The prepared ligands were treated with a palladium precursor to form the titled complexes ( 1–3 ) (Scheme 2). The synthesized complexes were obtained in good yields and are air stable and soluble in common solvents.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and structure of Pd(ii) pincer complexes: catalytic application in β-alkylation of secondary alcohols involving sequential dehydrogenation of alcohols via the borrowing hydrogen approach

Pranesh Kavin,

Ramesh

2023

Dalton Trans.

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“…Mp (62). 92 The title compound 62 was obtained as a white solid (118 mg, 61% yield from the reaction of β-bromostyrene with tris(4-tolyl)aluminum reagent and 80 mg, 41% yield from the reaction of 1-[(1E)-2-bromoethenyl]-4- 1-(1E)-1-Hexen-1-yl-4-methylbenzene (63). 94 The title compound 63 was obtained as colorless oil (87 mg, 50% yield) after purification by silica gel column chromatography.…”

Section: -Chloro-4-(4-methylphenyl)quinoline (20) 10bmentioning

confidence: 99%

General Copper-Catalyzed Coupling of Alkyl-, Aryl-, and Alkynylaluminum Reagents with Organohalides

et al. 2016

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We report the first example of a very general Cu-catalyzed cross-coupling of organoaluminum reagents with organohalides. The reactions proceed for the couplings of alkyl-, aryl-, and alkynylaluminum reagents with aryl and heteroaryl halides and vinyl bromides, affording the cross-coupled products in good to excellent yields. Both primary and secondary alkylaluminum reagents can be utilized as organometallic coupling partners. These reactions are not complicated by β-hydride elimination, and as a result rearranged products are not observed with secondary alkylaluminum reagents even for couplings with heteroaryl halides under "ligand-free" conditions. Radical clock experiment with a radical probe and relative reactivity study of Ph3Al with two haloarenes, 1-bromonaphthalene and 4-chlorobenzonitrile, having two different redox potentials indicates that the reaction does not involve free aryl radicals and radical anions as intermediates. These results combined with the result of the Hammett plot obtained by reacting Ph3Al with iodoarenes containing p-H, p-Me, p-F, and p-CF3 substituents, which shows a linear curve (R(2) = 0.99) with a ρ value of +1.06, suggest that the current transformation follows an oxidative addition-reductive elimination pathway.

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An efficient trifunctional benzhydrazone ligated Pd(II) complex for Heck reaction of aryl bromides

Cited by 24 publications

References 50 publications

Triphenylphosphinopalladium(II) complexes with ONO‐donor ligands: syntheses, structures and catalytic applications in CC cross‐coupling reactions

Triphenylphosphinopalladium(II) complexes with ONO‐donor ligands: syntheses, structures and catalytic applications in CC cross‐coupling reactions

Synthesis and structure of Pd(ii) pincer complexes: catalytic application in β-alkylation of secondary alcohols involving sequential dehydrogenation of alcohols via the borrowing hydrogen approach

General Copper-Catalyzed Coupling of Alkyl-, Aryl-, and Alkynylaluminum Reagents with Organohalides

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