1,2,3-triazole functionalized N-heterocyclic carbene binuclear nickel compound and preparation method thereof

A nitrogen-heterocyclic carbene and nickel compound technology, applied in the field of metal organic chemistry, can solve the problem of less research on dual-nuclear nickel compounds, and achieve the effects of novel structure, easy functionalization, and low equipment requirements

Inactive Publication Date: 2015-02-11
WUHAN TEXTILE UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nevertheless, in the published reports, the research on the binuclear nickel compounds supported by azacyclic carbene is still very little (Chinese patent CN201110241732, Zhou Y, Xi Z, Chen W, Wang D., Dinickel (II) Complexes of Bis ( N-heterocyclic carbene) Ligands Containing[Ni2(μ-OH)]Cores as Highly Efficient Catalysts for the Coupling of Aryl Chlorides, Organometallics, 2008, 27, 5911-5920; Xi Z, Zhou Y, Chen W., Efficient Negishi Coupling Reactions of Aryl Chlorides Catalyzed by Binuclear and Mononuclear Nickel-N-Heterocyclic Carbene Complexes, The Journal of Organic Chemistry, 2008, 73, 8497-8501), however the binuclear nickel carbene compounds reported above are limited to pyrazole functionalized compounds, 1, The preparation of 2,3-triazole-functionalized nitrogen-heterocyclic carbene binuclear nickel compounds and their application in catalytic cross-coupling reactions have not been reported yet

Method used

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  • 1,2,3-triazole functionalized N-heterocyclic carbene binuclear nickel compound and preparation method thereof
  • 1,2,3-triazole functionalized N-heterocyclic carbene binuclear nickel compound and preparation method thereof
  • 1,2,3-triazole functionalized N-heterocyclic carbene binuclear nickel compound and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0042]

[0043] At 50°C, add 1,2,3-triazole functionalized nitrogen heterocyclic carbene ligand L1 (477 mg, 1 mmol), silver oxide (116 mg, 0.5 mmol) and 20 mL of acetonitrile into a Schlenk reaction tube for 10 hours, then add NiCl 2 (PPh 3 ) 2 (654mg, 1mmol), stirred and reacted at 25°C for 6 hours, centrifuged to filter out the precipitate, concentrated the filtrate to 2mL, added 20mL of anhydrous ether, precipitated a solid, collected the solid by filtration, and vacuum-dried at 30°C for 10h to obtain the molecular structure: The 1,2,3-triazole functionalized azacyclic carbene binuclear nickel compound of 1 was 700 mg, and the yield was 55%. 1 H NMR (400MHz, d 6 -DMSO): δ8.54(b, 1H), 8.30(s, 1H), 7.89(t, J=7.2Hz, 1H), 7.79(s, 2H), 7.48(d, J=7.6Hz, 1H) ,7.39-7.33(m,6H),5.64(s,2H),5.68(s,4H)ppm. 13 C NMR (400MHz, d 6 -DMSO): δ156.9 (Ni-C), 153.9, 150.1, 141.2, 138.0, 137.5, 136.2, 129.3, 128.8, 125.1, 124.2, 123.9, 123.1, 123.0, 53.6, 53.5, 44.2ppm.

[0044] Utilizi...

Embodiment 2

[0048]

[0049] At 50°C, add 1,2,3-triazole functionalized nitrogen heterocyclic carbene ligand L2 (527mg, 1mmol), silver oxide (116mg, 0.5mmol) and 20mL of acetonitrile into the Schlenk reaction tube, react for 15 hours, then add NiCl 2 (PPh 3 ) 2 (654mg, 1mmol), stirred and reacted at 25°C for 7 hours, centrifuged to filter out the precipitate, concentrated the filtrate to 2mL, added 20mL of anhydrous ether, precipitated a solid, collected the solid by filtration, and vacuum dried at 30°C for 10h to obtain the molecular structure formula: The 1,2,3-triazole functionalized azacyclic carbene binuclear nickel compound of 2 was 714 mg, and the yield was 52%. 1 H NMR (400MHz, d 6 -DMSO): δ8.79(b,1H),8.46-8.44(m,1H),8.39(s,1H),8.29(t,J=8.0Hz,1H),8.18-8.16(m,1H), 8.06(d,J=8.0Hz,1H),7.78-7.72(m,3H),7.37-7.30(m,6H),5.98(s,2H),5.68(s,2H),5.63(s,2H) ppm. 13 C NMR (400MHz, d 6 -DMSO): δ157.9 (Ni-C), 153.9, 149.9, 147.6, 143.1, 141.1, 140.5, 136.2, 131.7, 130.1, 129.3, 128.8, 1...

Embodiment 3

[0054]

[0055] At 50°C, add 1,2,3-triazole functionalized nitrogen heterocyclic carbene ligand L3 (443mg, 1mmol), silver oxide (116mg, 0.5mmol) and 20mL of acetonitrile into the Schlenk reaction tube, react for 15 hours, then add NiCl 2 (PPh 3 ) 2 (654mg, 1mmol), stirred and reacted at 25°C for 8 hours, centrifuged to filter out the precipitate, concentrated the filtrate to 2mL, added 20mL of anhydrous ether, precipitated a solid, collected the solid by filtration, and vacuum dried at 30°C for 10h to obtain the molecular structure formula: The 1,2,3-triazole functionalized azacyclic carbene binuclear nickel compound of 3 was 747 mg, and the yield was 62%. 1 H NMR (400MHz, DMSO-d 6 ):δ9.05(s,1H,triazole),8.63(d,1H),8.16-8.14(m,2H),7.87(s,1H),7.82(s,1H),7.61-7.58(m,1H ),5.68(s,2H),5.65(s,2H),4.18(t,J=7.8Hz,2H),1.79-1.74(m,2H),1.31-1.24(m,2H),0.90(t, 3H,J=7.2Hz,). 13 C NMR (100MHz, DMSO-d 6 ): δ154.2 (Ni-C), 149.5, 148.7, 142.0, 136.8, 125.1, 123.2, 123.1, 122.5, 114.2...

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Abstract

The invention relates to a 1,2,3-triazole functionalized N-heterocyclic carbene binuclear nickel compound and a preparation method thereof and belongs to the field of organometallic chemistry. According to the 1,2,3-triazole functionalized N-heterocyclic carbene binuclear nickel compound, 1,2,3-triazole functionalized N-heterocyclic carbene is taken as a ligand, and the mole ratio of N-heterocyclic carbene to nickel is 1 to 1; the 1,2,3-triazole functionalized N-heterocyclic carbene binuclear nickel compound has a molecular structural formula shown in specification, wherein R1 is imidazole or benzimidazole, R2 is one of benzyl, n-butyl and phenyl, and X is either PF6 or BF4. The preparation method of the 1,2,3-triazole functionalized N-heterocyclic carbene binuclear nickel compound is simple, the binuclear nickel carbene compound is stable to air and moisture, and the distance among nickel atoms is relatively short, so that the compound has a metal-metal effect; by using the catalyst, cross-coupling reaction can be efficiently realized, and a variety of biphenyl derivatives can be obtained in the yield of being higher than 90%; the compound has very good functional group compatibility, is environment-friendly and can be extensively applied to fine chemical industry and pharmaceutical industry.

Description

technical field [0001] The invention relates to a 1,2,3-triazole functional nitrogen-heterocyclic carbene binuclear nickel compound and a preparation method thereof, belonging to the technical field of metal organic chemistry. Background technique [0002] In recent years, nitrogen heterocyclic carbene ligands have been used as supplements and substitutes of phosphine ligands due to their unique electronic properties and higher stability to heat and air than phosphine ligands, and are widely used in catalyzing various organic chemicals. In the reaction, especially the superior catalytic performance of bimetallic compounds has attracted great attention (Korbinian Riener, Stefan Haslinger, Andreas Raba, Manuel P. Mirza Cokoja, Wolfgang A. Herrmann, and Fritz E. Kühn, Chemistry of Iron N-Heterocyclic Carbene Complexes: Syntheses, Structures, Reactivities, and Catalytic Applications, Chem. Rev., 2014, 114, 5215–5272; Diez-Gonzalez, S., Marion, N., and Nolan, S.P.N-Heterocyclic...

Claims

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Application Information

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IPC IPC(8): C07F15/04B01J31/22C07B37/00C07C1/32C07C15/14C07C41/30C07C43/205C07D213/16C07D213/127
CPCB01J31/2217B01J2231/4233C07C1/326C07C41/30C07C2531/22C07D213/127C07D213/16C07F15/045C07C15/14C07C43/205
Inventor 顾绍金杜杰毫黄菁菁徐卫林夏欢徐灿红
Owner WUHAN TEXTILE UNIV
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