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Phosphite/N-heterocyclic carbene-containing mixed nickel (II) complex, and preparation method and application thereof

A nitrogen heterocyclic carbene and phosphite technology, applied in nickel complexes and in the field of organic synthesis, can solve problems such as no reports, no cross-coupling reaction of chlorinated hydrocarbons and neopentyl glycol biborates, etc. , to achieve the effect of easy product, conducive to large-scale synthesis and application, and high yield

Active Publication Date: 2016-08-17
东营悦来湖园区运营管理有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Compared with other phosphine ligands (such as triphenylphosphine and tricyclohexylphosphine), phosphite has lower price and lower toxicity, but so far, no phosphite and nitrogen-containing heterocycles have been seen. There is no report on the mixed nickel (II) complex of carbene, and there is no report on the cross-coupling reaction between chlorinated hydrocarbons and neopentyl glycol diboronate

Method used

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  • Phosphite/N-heterocyclic carbene-containing mixed nickel (II) complex, and preparation method and application thereof
  • Phosphite/N-heterocyclic carbene-containing mixed nickel (II) complex, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment one: Ni[P(OR 1 ) 3 ][(R 2 NCH 2 CH 2 NR 2 )C]X2 (R 1 = CH 2 CH 3 , R 2 =2,4,6-trimethylphenyl, X = Br) synthesis

[0026] The azacyclic carbene (R 2 NCH 2 CH 2 NR 2 )C (0.2464g, 0.8 mmol) was added into a tetrahydrofuran solution of di(triethylphosphite)nickel(II) bromide (0.4400 g, 0.8 mmol), reacted at room temperature for 2 hours, and removed the solvent in vacuo, Wash the residue with n-hexane, extract the residue with toluene, transfer the clear liquid and remove the solvent toluene to obtain a red solid with a yield of 68%.

[0027] The product was subjected to elemental analysis, and the results are shown in Table 1:

[0028] Table 1 Elemental analysis results

[0029]

C：（%）

H：（%）

N：（%）

theoretical value

46.86

6.12

4.05

actual value

47.04

6.21

3.99

[0030] The product was characterized by NMR, and the results are as follows:

[0031] Dissolve the product in C 6 D. 6 Medium (abo...

Embodiment 2

[0032] Embodiment two: Ni[P(OR 1 ) 3 ][(R 2 NCH 2 CH 2 NR 2 )C]X 2 (R 1 = CH 2 CH 3 , R 2 = 2,6-Diisopropylphenyl, X = Br) Synthesis of

[0033] The azacyclic carbene (R 2 NCH 2 CH 2 NR 2 )C (0.3627 g, 0.93 mmol) was added into a tetrahydrofuran solution of two (triethyl phosphite) nickel (II) bromide (0.5115 g, 0.93 mmol), reacted at room temperature for 2 hours, and removed the solvent in vacuo, Wash the residue with n-hexane, extract the residue with toluene, transfer the clear liquid and remove the solvent toluene to obtain a red solid with a yield of 77%.

[0034] Product is carried out elemental analysis, and the result is as shown in table 2:

[0035] Table 2 Elemental Analysis

[0036]

C：（%）

H：（%）

N：（%）

theoretical value

51.06

7.01

3.61

actual value

51.33

7.19

3.49

[0037] The product was characterized by NMR, and the results are as follows:

[0038] Dissolve the product in C 6 D. 6 Medium (a...

Embodiment 3

[0039] Embodiment three: Ni[P(OR 1 ) 3 ][(R 2 NCH 2 CH 2 NR 2 )C]X 2 (R 1 = CH(CH 3 ) 2 , R 2 = 2,6-Diisopropylphenyl, X = Br) Synthesis of

[0040] The azacyclic carbene (R 2 NCH 2 CH 2 NR 2 )C (0.3627 g, 0.93 mmol) was added to a tetrahydrofuran solution of di(triisopropyl phosphite) nickel(II) bromide (0.5905 g, 0.93 mmol), reacted at room temperature for 3 hours, and removed the solvent in vacuo , wash the residue with n-hexane, extract the residue with toluene, transfer the clear liquid and remove the solvent toluene to obtain a red-black solid with a yield of 70%.

[0041] Product is carried out elemental analysis, and the result is as shown in table 3:

[0042] Table 3 Elemental analysis

[0043]

C：（%）

H：（%）

N：（%）

theoretical value

52.84

7.39

3.42

actual value

53.11

7.51

3.28

[0044] The product was characterized by NMR, and the results are as follows:

[0045] Dissolve the product in C 6 D. 6...

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Abstract

The invention discloses a phosphite / N-heterocyclic carbene-containing mixed nickel (II) complex, and a preparation method and application thereof. The chemical formula of the mixed nickel (II) complex is Ni[P(OR1)3][(R2NCH2CH2NR2)C]X2. The phosphite / N-heterocyclic carbene-containing mixed nickel (II) complex can efficiently catalyze cross coupling reaction between chlorohydrocarbon and neopentyl glycol biborate in the presence of potassium methoxide to prepare the neopentyl glycol arylborate, which is an example of the cross coupling reaction catalyzed by the mixed nickel (II) complex by using phosphite and N-heterocyclic carbene as auxiliary ligands.

Description

technical field [0001] The invention relates to a nickel (II) complex and its application in the field of organic synthesis, in particular to a mixed nickel (II) complex containing phosphite and nitrogen heterocyclic carbene, its preparation method and its Application as a one-component catalyst in the cross-coupling reaction of chlorinated hydrocarbons and neopentyl glycol biborate. Background technique [0002] Aryl boronic acid ester compounds are a very important synthetic intermediate in the field of organic synthesis, so how to synthesize various aryl boronic acid ester compounds simply and efficiently has received continuous attention (see: Boronic Acids; Hall, D. G.; Wiley-VCH: Weinheim, Germany, 2005). The traditional method of synthesizing aryl borate compounds is to react halogenated hydrocarbons and trialkyl borates under the action of metal organic reagents (such as organozinc reagents, Grignard reagents), but this method needs to use sensitive metalorganic re...

Claims

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Application Information

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IPC IPC(8): C07F15/04C07F5/02B01J31/22
CPCB01J31/185B01J31/2273B01J2231/4277B01J2531/0233B01J2531/847C07F5/02C07F15/04
Inventor 孙宏枚许槿张杰
Owner 东营悦来湖园区运营管理有限公司
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