Synthesis of novel 1-alkylimidazoline and 1-alkylbenzimidazole palladium(II) complexes as efficient catalysts for Heck and Suzuki reactions involving arylchlorides

Özdemır, İsmaıl; Çetınkaya, Bekır; Demır, Serpıl

doi:10.1016/j.molcata.2003.07.010

Cited by 34 publications

(5 citation statements)

References 35 publications

(25 reference statements)

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“…The NMR and IR values are similar to those found for N-coordinated metal complexes [18][19][20][21][22][23][24]. The NMR and IR values are similar to those found for N-coordinated metal complexes [18][19][20][21][22][23][24].…”

Section: Resultssupporting

confidence: 83%

Synthesis of Pd(II) 1-alkylperimidine complexes as efficient catalysts for suzuki reactions involving arylchlorides

�zdemir¹,

Al�c�²,

G�rb�z

et al. 2005

Russ J Coord Chem

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Three palladium(II) complexes of the type [PdCl 2 ( PPh 3 ) L] (L-1-alkylperimidine) have been prepared by reactions of [ PdCl 2 ( PR 3 )] 2 with 1-alkylperimidine. The complexes were characterized by conventional spectroscopic methods and elemental analyses. The incorporation of N-coordinated perimidine complexes of palladium(II) gave high catalytic activity in the Suzuki coupling deactivated aryl chloride substrates.

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Section: Resultssupporting

confidence: 83%

Synthesis of Pd(II) 1-alkylperimidine complexes as efficient catalysts for suzuki reactions involving arylchlorides

�zdemir¹,

Al�c�²,

G�rb�z

et al. 2005

Russ J Coord Chem

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“…The NMR and IR values are similar to those found for N-coordinated metal complexes [18][19][20][21][22][23][24].…”

Section: Resultssupporting

confidence: 79%

“…Recently, we have developed improved procedures of Heck and Suzuki reactions of aryl chlorides making use of novel ligands 1,3-bis(2,4,6-trimethylbenzyl)imidazolium chloride, 1-alkylimidazoline, α -bis(imine) [23,24]. The 1-alkylperimidine complexes are insensitive to air and moisture and are thermally stable in both the solid state and in solution.…”

Section: R Rmentioning

confidence: 99%

Synthesis of Pd(II) 1-alkylperimidine complexes as efficient catalysts for Suzuki reactions involving arylchlorides

et al. 2005

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Interaction of aryl halides with arylboronic acids (via Suzuki reaction) representing one of the most general C-C coupling reactions in organic synthesis, is catalyzed by palladium complexes in homogeneous solution according to the following equation [1][2][3]:(1)The reactivity of the aryl halide component decreases drastically in the X order I > Br > Cl and electron-withdrawing substituents R are required for the chlorides to react [1][2][3][4][5][6]. The low reactivity of aryl chlorides in cross-coupling reactions is generally ascribed to their reluctance to oxidatively add to Pd(0) [4][5][6]. Current interest focuses on the use of aryl chlorides since they are cheaper and more readily accessible than bromides and iodides [7]. Significant advances have been recently achieved by use of palladacycles and especially, by use of bulky and electron-rich tertiary phosphines as catalyst modifiers systems [8][9][10][11][12][13][14]. However, the major drawback of these is that the phosphine ligands are comparatively difficult to make or rather expensive. Furthermore, tertiary phosphines require airfree handling to prevent their oxidation and are susceptible to P-C bond cleavage at elevated temperatures [15].On the other hand, transition metal complexes with ligands containing nitrogen-donor atoms have been shown their potential to successfully promote the catalytic transformation of organic compounds [16,17]. These discoveries motivate the search for the new metal complexes with N-coordinated ligands and the evaluation of their catalytic properties.] Base X = Cl, Br, I. R ROur contribution to this field has started with syntheses of 2-imidazoline and benzimidazole complexes of Pt(II), Rh(I), Ru(II), and Pd(II) which are capable of catalyzing the cyclopropanation of styrene with ethyl diazoacetate and intramolecular cyclization of (Z)-3-methylpent-2-en-4-yn-1-ol into 2,3-dimethylfuran in good yields [18][19][20][21][22]. Recently, we have developed improved procedures of Heck and Suzuki reactions of aryl chlorides making use of novel ligands 1,3-bis(2,4,6-trimethylbenzyl)imidazolium chloride, 1-alkylimidazoline, α -bis(imine) [23,24]. The 1-alkylperimidine complexes are insensitive to air and moisture and are thermally stable in both the solid state and in solution.However, the development of new ligands or the application of existing ligands in Suzuki reaction, particularly those involving aryl chlorides as substrates, is still of considerable importance.We report here the straightforward preparation of a series phosphine palladium complexes with N-coordinated 1-alkylperimidine derivatives. These complexes were shown to be effective catalysts for Suzuki reaction especially with arylchlorides. EXPERIMENTALAll reactions were performed using Schlenk-type flask under argon and standard high vacuum-line techniques. Solvents were analytical grade and distilled under argon from sodium benzophenone (Et 2 O, dioxane, toluene, n -hexane ). 1 -Substituted perimidine (A) were prepared according to the literature [25,26]. NMR spectr...

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“…They showed that the catalytic activity was associated with the N-substitution on the imidazole. From a catalytic point of view, the ligating imidazole nitrogen also has a tunable basicity which makes them attractive as ligands for catalysts [7][8][9]. It was shown that a change in ligand basicity has a marked effect on metal-ligand bond strengths, which in turn affect the catalytic properties [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

“…From a catalytic point of view, the ligating imidazole nitrogen also has a tunable basicity which makes them attractive as ligands for catalysts [7][8][9]. It was shown that a change in ligand basicity has a marked effect on metal-ligand bond strengths, which in turn affect the catalytic properties [6][7][8][9]. Apart from catalysis, the metal binding properties of imidazole-based ligands have been explored in detail due to their presence at the active site of metallo-proteins or enzymes involved in several important metabolic processes [10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of palladium(II) and platinum(II) complexes with ferrocenylimidazole

Nyamori

Onyancha

McCleland

et al. 2009

Journal of Organometallic Chemistry

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Synthesis of novel 1-alkylimidazoline and 1-alkylbenzimidazole palladium(II) complexes as efficient catalysts for Heck and Suzuki reactions involving arylchlorides

Cited by 34 publications

References 35 publications

Synthesis of Pd(II) 1-alkylperimidine complexes as efficient catalysts for suzuki reactions involving arylchlorides

Synthesis of Pd(II) 1-alkylperimidine complexes as efficient catalysts for suzuki reactions involving arylchlorides

Synthesis of Pd(II) 1-alkylperimidine complexes as efficient catalysts for Suzuki reactions involving arylchlorides

Synthesis and characterization of palladium(II) and platinum(II) complexes with ferrocenylimidazole

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