Ionic liquid type monophosphine monoimidazolium salt nickel (II) complex and preparation and application thereof

A single imidazolium salt and ionic liquid technology, applied in the field of nickel complexes, can solve the problems of difficult synthesis and instability of imidazolium salts, and achieve the effects of rich structural changes, easy products and high yields

Inactive Publication Date: 2009-12-02
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such organophosphine-functionalized imidazoliu

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment one: (Ph 3 P)Ni{[(RNCHCHNR)CH]X}X 2 ; R is the synthesis of isopropyl (taking X=Cl as an example)

[0038] [(RNCHCHNR)CH]Cl (0.19 g, 1.0 mmol) was added to (Ph 3 P) 2 NiCl 2 (0.65 g, 1.0 mmol) in tetrahydrofuran solution, stirred and reacted at 45°C for 2 hours, removed the solvent, washed with hexane, drained, extracted with a mixed solution of tetrahydrofuran and toluene, transferred the centrifuged supernatant, concentrated, and obtained at room temperature Blue crystals were precipitated with a yield of 75%.

Embodiment 2

[0039] Embodiment two: (Ph 3 P)Ni{[(RNCHCHNR)CH]X}X 2 ; R is the synthesis of 2,6-diisopropylphenyl (taking X=Cl as an example)

[0040] [(RNCHCHNR)CH]Cl (0.43 g, 1.0 mmol) was added to (Ph 3P) 2 NiCl 2 (0.65 g, 1.0 mmol) in tetrahydrofuran solution, stirred and reacted at 45°C for 6 hours, removed the solvent, washed with hexane, drained, extracted with a mixed solution of tetrahydrofuran and toluene, transferred the centrifuged supernatant, concentrated, and dried at room temperature Blue crystals were precipitated with a yield of 60%.

Embodiment 3

[0041] Embodiment three: (Ph 3 P)Ni{[(RNCHCHNR)CH]X}X 2 ; R is the synthesis of isopropyl (taking X=Br as an example)

[0042] [(RNCHCHNR)CH]Br (0.23 g, 1.0 mmol) and NaBr (0.224 g, 2.2 mmol) were added to (Ph 3 P) 2 NiCl 2 (0.65 g, 1.0 mmol) in tetrahydrofuran solution, stirred and reacted at 45°C for 4 hours, removed the solvent, washed with hexane, drained, extracted with a mixed solution of tetrahydrofuran and toluene, transferred the centrifuged supernatant, concentrated, and dried at room temperature Green crystals were precipitated with a yield of 72%.

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PUM

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Abstract

The invention discloses an ionic liquid type monophosphine monoimidazolium salt nickel (II) complex and preparation and application thereof. The chemical molecular formula of the monophosphine monoimidazolium salt nickel (II) complex is (Ph3P)Ni{[(RNCHCHNR)CH]X}X2, wherein R is selected from one of C1-C4 saturated alkyl, phenmethyl, 2,6-diisopropylphenyl and mesitylene; and X is halogen and selected from one of chlorine, bromine or iodine. The monophosphine monoimidazolium salt nickel (II) complex has good catalytic activity on Kumada cross-coupling reaction between aryl Grignard reagent and aryl halide or halogenated pyridine.

Description

technical field [0001] The invention relates to a nickel complex, in particular to an ionic liquid type monophosphine monoimidazolium salt nickel (II) complex. Background technique [0002] Nickel-based catalysts have obvious advantages over palladium-based catalysts in industrial applications due to their low price, easy synthesis, good tolerance and high catalytic activity, and have received increasing attention in the past decade. In 2006, Matsubara's research group unexpectedly obtained a monophosphine mononitroheterocyclic carbene nickel (II) complex when reacting bis(triphenylphosphine) nickel (II) dichloride with in-situ generated nitrogen heterocyclic carbene (See: Matsubara, K.; Ueno, K.; Shibata, Y. Organometallics 2006, 25, 3422), the study found that this complex has good catalytic performance in Kumada cross-coupling reaction and C-N cross-coupling reaction Activity (see: Matsubara, K.; Ueno, K.; Shibata, Y.Organometallics 2006,25,3422; Matsubara, K.; Ueno, K.;...

Claims

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Application Information

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IPC IPC(8): C07F19/00C07F15/04B01J31/24C07B49/00C07C15/14C07D213/16C07D213/127
Inventor 孙宏枚谢玲芝刘志宏沈琪
Owner SUZHOU UNIV
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