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Method for preparing arylboronic acid neopentyl glycol ester compound

A technology for neopentyl glycol diboronic acid esters and ester compounds, which is applied in the field of preparing neopentyl glycol boric acid ester compounds, and can solve the problem of unreported, unseen chlorinated hydrocarbons and neopentyl glycol diboronic acid esters. Problems such as cross-coupling reaction, to achieve the effect of simple and easy operation, easy product and high yield

Active Publication Date: 2018-05-01
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] 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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  • Method for preparing arylboronic acid neopentyl glycol ester compound
  • Method for preparing arylboronic acid neopentyl glycol ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 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

[0027] 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%.

[0028] The product was subjected to elemental analysis, and the results are shown in Table 1:

[0029] Table 1 Elemental analysis results

[0030]

C：（%）

H：（%）

N：（%）

theoretical value

46.86

6.12

4.05

actual value

47.04

6.21

3.99

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

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

Embodiment 2

[0033] 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

[0034] 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%.

[0035] Product is carried out elemental analysis, and the result is as shown in table 2:

[0036] Table 2 Elemental analysis

[0037]

C：（%）

H：（%）

N：（%）

theoretical value

51.06

7.01

3.61

actual value

51.33

7.19

3.49

[0038] The product was characterized by NMR, and the results are as follows:

[0039] Dissolve the product in C 6 D. 6 Medium (a...

Embodiment 3

[0040] 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

[0041] 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%.

[0042] Product is carried out elemental analysis, and the result is as shown in table 3:

[0043] Table 3 Elemental analysis

[0044]

C：（%）

H：（%）

N：（%）

theoretical value

52.84

7.39

3.42

actual value

53.11

7.51

3.28

[0045] The product was characterized by NMR, and the results are as follows:

[0046] Dissolve the product in C 6 D. 6...

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Abstract

The invention discloses a method for preparing an arylboronic acid neopentyl glycol ester compound. A chemical formula of a catalyst mixed type nickel (II) coordination compound is Ni[P(OR1)3][(R2NCH2CH2NR2)C]X2. The mixed type nickel (II) coordination compound containing a phosphite ester and n-heterocyclic carbene can be used for high-efficiently catalyzing cross coupling reaction of a hydrochloric ether and bisdiboron with the existence of potassium methoxide so as to prepare the arylboronic acid neopentyl glycol ester compound. The invention provides the first case by adopting the mixed type nickel (II) coordination compound taking the phosphite ester and the n-heterocyclic carbene as auxiliary ligands for catalyzing the cross coupling reaction.

Description

[0001] The invention belongs to the mixed nickel (II) complex containing phosphite and nitrogen heterocyclic carbene, its preparation method and application. The application number is 201610215681.2, and the application date is April 8, 2016, which is the branch of the invention patent. Case application, which belongs to the preparation technology part of the compound. technical field [0002] The invention relates to a nickel (II) complex and its application in the field of organic synthesis, in particular to a method for preparing neopentyl glycol arylboronic acid ester compounds. Background technique [0003] Arylboronate compounds are very important synthetic intermediates in the field of organic synthesis, so how to synthesize various arylboronate 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 h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F15/04B01J31/22
CPCB01J31/185B01J31/2273B01J2231/4277B01J2531/0233B01J2531/847C07F5/02C07F15/04
Inventor 孙宏枚许槿张杰
Owner SUZHOU UNIV
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