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Method for preparing arylboronic acid neopentyl glycol ester

A technology of neopentyl glycol diboronic acid ester and neopentyl glycol ester, which is applied in the field of preparing neopentyl glycol diboronic acid ester, and can solve the cross-coupling reaction between chlorinated aromatic hydrocarbons and neopentyl glycol diboronic acid ester that has not been seen and other issues, to achieve the effects of large-scale synthesis and application, high yield and easy product

Active Publication Date: 2016-07-06
HUAWEI TEHCHNOLOGIES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there have been no reports of mixed nickel(II) complexes containing phosphite and azacyclic carbene, nor have they catalyzed the cross-coupling between chlorinated arenes and neopentyl glycol diboronate reaction to reports

Method used

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  • Method for preparing arylboronic acid neopentyl glycol ester
  • Method for preparing arylboronic acid neopentyl glycol ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment one: Ni[P(OR 1 ) 3 ][(R 2 NCH 2 CH 2 NR 2 )C]X 2 (R 1 =CH 2 CH 3 , R 2 =2,4,6-trimethylphenyl, X=Br) synthesis

[0020] The azacyclic carbene (R 2 NCH 2 CH 2 NR 2 )C (0.2464g, 0.8 mmol) was added to a THF solution of bis(triethylphosphite) nickel dibromide (0.4400 g, 0.8 mmol), reacted at room temperature for 2 hours, removed the solvent in vacuo, and washed with n-hexane The residue was extracted with toluene, the clear liquid was transferred and the solvent toluene was removed to obtain a red solid with a yield of 68%.

[0021] The product was subjected to elemental analysis, and the results are shown in Table 1:

[0022] Table 1 Elemental analysis results

[0023]

C：（%）

H：（%）

N：（%）

theoretical value

46.86

6.12

4.05

actual value

47.04

6.21

3.99

[0024] The product was characterized by NMR, and the results are as follows:

[0025] Dissolve the product in C 6 D. 6 Medium (a...

Embodiment 2

[0026] 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

[0027] 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(triethylphosphite)nickel dibromide (0.5115 g, 0.93 mmol), reacted at room temperature for 2 hours, removed the solvent in vacuo, and washed with n-hexane Wash the residue, extract the residue with toluene, transfer the clear liquid and remove the solvent toluene to obtain red crystals with a yield of 77%.

[0028] Product is carried out elemental analysis, and the result is as shown in table 2:

[0029] Table 2 Elemental analysis

[0030]

C：（%）

H：（%）

N：（%）

theoretical value

51.06

7.01

3.61

actual value

51.33

7.19

3.49

[0031] The product was characterized by NMR, and the results are as follows:

[0032] Dissolve the product in C 6 D. 6 Medium (a...

Embodiment 3

[0033] 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

[0034] 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 dibromide (0.5905 g, 0.93 mmol), and reacted at room temperature for 3 hours, and the solvent was removed in vacuo, and the Wash the residue with alkane, extract the residue with toluene, transfer the clear liquid and remove the solvent toluene to obtain red and black crystals with a yield of 70%.

[0035] Product is carried out elemental analysis, and the result is as shown in table 3:

[0036] Table 3 elemental analysis

[0037]

[0038] The product was characterized by NMR, and the results are as follows: the product was dissolved in C 6 D. 6 Medium (about 0.4mL), seal the tube, measure and characterize on a UnityInova-400 NMR instrument at room temperature: 1 HNM...

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Abstract

The invention discloses a method for preparing arylboronic acid neopentyl glycol ester.The method includes the steps that a mixed-type nickel (II) complex with Ni(P(OR1)3)((R2NCH2CH2NR2)C)X2 as the chemical formula serves as a catalyst, and a cross coupling reaction of phenyl chlorine substitutes and bis(neopentyl glycolato) diboron is efficiently catalyzed in potassium methoxide to prepare the arylboronic acid neopentyl glycol ester.The method is the first case that the mixed-type nickel (II) complex catalyzes the cross coupling reaction with phosphite ester and n-heterocyclic carbine as auxiliary ligands.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing neopentyl glycol aryl borate. Background technique [0002] Arylboronic ester compounds are a very important synthetic intermediate in the field of organic synthesis, so how to synthesize various arylboronic acid ester compounds simply and efficiently has received continuous attention (see: BoronicAcids; Hall, D.G.; Wiley -VCH: Weinheim, Germany, 2005). The traditional method of synthesizing aryl borates is to react halogenated aromatic hydrocarbons and trialkyl borates under the action of metal organic reagents (such as organozinc reagents, Grignard reagents), but this method needs to use sensitive metals There are many restrictions on organic reagents (see: Suzuki, A.; Brown, H.C. Organic Syntheses via Boranes; Aldrich Chemical Co.: Milwaukee, 2003; Vol.3). In order to avoid the use of the above-mentioned organometallic reagents, p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F15/04B01J31/22
CPCB01J31/185B01J31/2273B01J2231/4277B01J2531/847C07F5/025C07F15/04
Inventor 孙宏枚许槿
Owner HUAWEI TEHCHNOLOGIES CO LTD
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