Bis(triphenylphosphine)palladium(II)phthalimide – an easily prepared precatalyst for efficient Suzuki–Miyaura coupling of aryl bromides

Chaignon, Nicholas M.; Fairlamb, Ian J. S.; Kapdi, Anant R.; Taylor, Richard J.K.; Whitwood, Adrian C.

doi:10.1016/j.molcata.2004.05.008

Cited by 33 publications

(17 citation statements)

References 66 publications

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“…The Pd-O distances are in the range 1.979(3) -2.008(4) Å with Pd-N distances 1.981(3) -2.014(3) Å, which are typical of the square-planar Pd II complex of Schiff base ligand [7]. The bond angles around Pd II ions suggested that the complex has a distorted square-planar geometry as indicated by the angles O-Pd-O in the range 79.66(11) -80.54(16), O-Pd-N in the range 92.14(13) -92.95 (11) and N-Pd-N in the range 94.92(12) -94.95(15), deviating substantially from that expected for a regular squareplanar geometry.…”

Section: X-ray Crystallography Analysismentioning

confidence: 96%

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Symmetrical Palladium (II) N,N,O,O-Schiff Base Complex: Efficient Catalyst for Heck and Suzuki Reactions

Ibrahim¹,

Shamsuddin²

2012

CSTA

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Palladium is arguably the most versatile and most widely applied catalytic metal in the field of fine chemicals due to its high selectivity and activity. Palladium catalyst offers an abundance of possibilities of carbon-carbon bond formation in organic synthesis. In this research, three different Schiff base ligands have been prepared by condensation reaction between appropriate aldehyde or ketone with amine namely 2,2-dimethyl-1,3-propanediamine in the molar ratio of 2:1. The corresponding palladium (II) Schiff base complexes were prepared through the reaction between the Schiff base ligand with palladium (II) acetate in a molar ratio 1:1. FTIR, 1 H-NMR and 13 C-NMR spectroscopic data revealed that the ligands are N,N,O,O-tetradentate coordinated to the Pd atom through both the azomethine N atoms and phenolic O atoms. From X-ray Crystallographic analysis, it showed that the complex exists as square planar geometry. The synthesized palladium (II) Schiff base complexes were then subjected in catalytic Heck and Suzuki reaction of iodobenzene.

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Section: X-ray Crystallography Analysismentioning

confidence: 96%

“…The type of bases was chosen based on their performance in Suzuki reaction to form similar biphenyl products [10,11]. In Suzuki reaction, the presence of base is needed since the cross coupling via transmetallation step is difficult due to the low nucleophilicity of organic groups (R) on the boron atom.…”

Section: Effect Of Basesmentioning

confidence: 99%

Symmetrical Palladium (II) N,N,O,O-Schiff Base Complex: Efficient Catalyst for Heck and Suzuki Reactions

Ibrahim¹,

Shamsuddin²

2012

CSTA

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“…1 They have become of interest in recent years for applications as electrical insulators, alignment films for liquid crystal displays, 2 biomaterials as well as in medical and sensor technology [3][4][5] and electronics, [6][7][8] because of their easy process ability, low dielectric constant, their outstanding thermal and mechanical properties.…”

Section: Introductionmentioning

confidence: 99%

Determination of optical constants of poly(<I>N</I>-phthalimidomethyl methacrylate)

Kaya¹,

Gündüz²

2015

Mat Express

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The polymer of N-phthalimidomethyl methacrylate (PNPMMA) was synthesized by free radical polymerization. The poly(PNPMMA) is significant material, because it is a soluble material. The poly(PNPMMA) exhibits a low transmittance behavior in the visible region. The band gap of the poly(PNPMMA) thin film was found to be 1.62 eV. The refractive index value of the poly(PNPMMA) varies between 3.00 and 1.56. The plot of refractive index is composed of two regions so-called normal and abnormal dispersion. We calculated many optical parameters such as average transmittance, absorption band edge, refractive index, incidence and refraction angle, direct and indirect band gap, real and imaginary parts of dielectric constant, real part and imaginary parts of the optical conductivity of the poly(PNPMMA). The poly(PNPMMA) is a semiconductor and it can be used in the fabrication of the metal-semiconductor (MS) contacts like Schottky diode due to low optical band gap and suitable optical contacts and it is significant material in applications of some devices such as an image sensor packaging structure and high intensity medium-pressure lamps due to low transmittance values in the visible region.

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“…Nevertheless, the coordination chemistry of phthalimide is little developed, comprising only a few structurally characterized complexes of mainly some group eight metals as well as Au, Cu, Zn and Mn [2] which, however, are of potential interest in e.g. catalysis, fluorescence, medicinal chemistry and magnetism [3][4][5][6][7][8].Within our ongoing research focused on the metal-promoted activations of nitriles [9-13], we have recently reported the Ni(II)-ketoxime mediated transformations of different nitriles (RCN, R = alkyl, aryl) or/and phthalonitriles to afford various nickel-ligated species which include (i) symmetrical imidoylamidines (1,3,5-triazapentadienes) [14], (ii) phthalocyanines [15] and (iii) unsymmetrical imidoylamidines with imino-isoindolinone moieties [16]. In particular, it has been found [15][16][17] that the formation of the products listed in (ii) and (iii) proceeds through uncommon intermediates, e.g.…”

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confidence: 99%

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confidence: 99%

Novel nickel(II) complex bearing phthalimido ligands derived from oxime-mediated transformation of phthalonitrile

Kopylovich¹,

Haukka

Kirillov³

et al. 2008

Inorganic Chemistry Communications

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Bis(triphenylphosphine)palladium(II)phthalimide – an easily prepared precatalyst for efficient Suzuki–Miyaura coupling of aryl bromides

Cited by 33 publications

References 66 publications

Symmetrical Palladium (II) N,N,O,O-Schiff Base Complex: Efficient Catalyst for Heck and Suzuki Reactions

Symmetrical Palladium (II) N,N,O,O-Schiff Base Complex: Efficient Catalyst for Heck and Suzuki Reactions

Determination of optical constants of poly(<I>N</I>-phthalimidomethyl methacrylate)

Novel nickel(II) complex bearing phthalimido ligands derived from oxime-mediated transformation of phthalonitrile

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