Synthesis and Structural Characterization of Monophosphine-Cyclopalladated Ferrocenylpyrimidine Complexes and Reusable Catalytic System for Amination of Hindered Aryl Chlorides in PEG-400

Xu, Chen; Wang, Zhiqiang; Fu, Weijun; Liu, Xinhua; Li, Yingfei; Cen, Fei-Fei; Ma, Hongyang; Ji, Baoming

doi:10.1021/om801149r

Cited by 58 publications

(31 citation statements)

References 74 publications

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“…Among them,cyclopalladated complexes containing N-donor ferrocenylligand have been studied extensively in the past two decades [6,7]. We have studied the cyclopalladation of ferrocenyl ligand containing N-donor and coupling reaction of chloromercuriferrocene [8][9][10].T he coupling reaction with chloromercuriferrocene and 2,5-dibromopyridine readily afforded the title compound. Two cyclopentadienyl rings in the title crystal structure are almost parallel with dihedral angles of 1.8°.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (5-bromo-2-pyridyl)ferrocene, C15H12BrFeN

Ma¹,

Wang²,

Li³

et al. 2012

Zeitschrift Für Kristallographie - New Crystal Structures

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Section: Discussionmentioning

confidence: 99%

Crystal structure of (5-bromo-2-pyridyl)ferrocene, C15H12BrFeN

Ma¹,

Wang²,

Li³

et al. 2012

Zeitschrift Für Kristallographie - New Crystal Structures

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“…In addition, there are two types of intermolecular p-p stacking interactions. One p-p stacking interaction is between the pyrimidine rings of the two chains (the interplane distance is 3.414 Å) [ 8]. The other p-p stacking interaction is pyrimidine ring and benzimidazole ring (the interplane distance 3.593 Å), which link the molecules into alayers.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(4,6-dimethylpyrimidin-2-yl)benzimidazole, C13H12N4

Li¹,

Xu²,

Liu³

et al. 2011

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C 13 H 12 N 4 ,monoclinic, P12 1 /c1(no. 14), a =8.682(1) Å, Source of materialBenzimidazole (3 mmol) and NaH (9 mmol) were dissolved in dry dioxane (25 ml) and the solution was stirred for 2hatroom temperature, then 4,6-dimethyliodopyrimidine (3 mmol) was added. The resultant solution was heated to reflux for 6h,removal of solvent resulted in awhite powder that was recrystallized from dichloromethane/petroleum ether solution at room temperature to give the desired crystals suitable for single crystal X-ray diffraction.

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“…Among them, cyclopalladated complexes containing N-donor ferrocenyl ligand have been studied extensively in the past two decades [4][5][6]. In addition, the oxime-based palladacycles are air and water stable effective pre-catalysts for a wide range of coupling processes such as Heck and Hiyama reactions in aqueous solution [7,8].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (acetylferrocene oxime-κ2C9,N)chloro- (tricyclohexylphosphine-κP)palladium(II), PdCl[(C7H7NO)Fe(C5H5)][P(C6H11)3]

Bai¹,

Liu²,

Li³

et al. 2010

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Source of materialThe title compound was prepared as described in literature [1], using tricyclohexylphosphine instead of triphenylphosphine and recrystallized from dichloromethane/petroleum ether solution at room temperature to give the desired crystals suitable for singlecrystal X-ray diffraction investigation. Experimental detailsH1A bound to oxygen atom was found in difference Fourier map and refined freely. The other hydrogen atoms bound to carbon atoms were placed in geometrically idealized positions and treated as riding with d(C-H) =0.93 -0.96 Å,and with U iso(H) = 1.2 U eq (C) or 1.5 U eq (C methyl ). DiscussionIn the palladium-catalyzed coupling reactions, palladacycles have shown enormous superiority in many respects due to their ready preparation, facile modification, high activity and comparative stability [2,3]. Among them, cyclopalladated complexes containing N-donor ferrocenyl ligand have been studied extensively in the past two decades [4][5][6]. In addition, the oxime-based palladacycles are air and water stable effective pre-catalysts for a wide range of coupling processes such as Heck and Hiyama reactions in aqueous solution [7,8].The Pd atom in the title complex is in aslightly distorted squareplanar environment bonded to the phosphorus, the nitrogen, the carbon atom of the ferrocenyl moiety and the chloride anion. The ferrocenyl fragment and the -OH group are in a trans arrangement [torsion angle C10-C10-N1-O1 =178.9 (4) . In the crystal structure there exist C-H···Cl (2.903 Å)and C-H···O(2.611 Å)hydrogen bonds between the chloride (oxygen) atom and the adjacent C-H group of the cyclohexane ring [9], which are realized the chain structure of the title compound.

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Synthesis and Structural Characterization of Monophosphine-Cyclopalladated Ferrocenylpyrimidine Complexes and Reusable Catalytic System for Amination of Hindered Aryl Chlorides in PEG-400

Cited by 58 publications

References 74 publications

Crystal structure of (5-bromo-2-pyridyl)ferrocene, C15H12BrFeN

Crystal structure of (5-bromo-2-pyridyl)ferrocene, C15H12BrFeN

Crystal structure of 1-(4,6-dimethylpyrimidin-2-yl)benzimidazole, C13H12N4

Crystal structure of (acetylferrocene oxime-κ2C9,N)chloro- (tricyclohexylphosphine-κP)palladium(II), PdCl[(C7H7NO)Fe(C5H5)][P(C6H11)3]

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