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Method for preparing borate by utilizing p-toluidine lithium

A methylaniline, borate ester technology, applied in chemical instruments and methods, compounds containing periodic table Group 3/13 elements, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problem of expensive catalysts. , harsh reaction conditions and other problems, to achieve the effect of good universality, short reaction time and high catalytic activity

Inactive Publication Date: 2018-08-07
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in the catalytic systems reported so far, the catalysts are relatively expensive, or the reaction conditions are relatively harsh.

Method used

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  • Method for preparing borate by utilizing p-toluidine lithium
  • Method for preparing borate by utilizing p-toluidine lithium
  • Method for preparing borate by utilizing p-toluidine lithium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Hydroboration reaction of acetophenone and pinacol borane catalyzed by p-methylanilinide lithium

[0028] In the reaction flask that has been dehydrated and deoxygenated, under the protection of argon, add 20ul of tetrahydrofuran solution (0.05M) of p-methylanilinide lithium (0.1 mol% dosage), then add 0.1596 mL of borane with a syringe, mix well, and then use 0.117 mL of acetophenone was added into the syringe, and the mixture was stirred at room temperature. After 20 min of reaction, the NMR yield was 99%. After that, a small amount of tetrahydrofuran and excess borane were removed under reduced pressure to obtain the corresponding pinacol borate. C 6 h 5 CH(CH 3 )OB(OC(CH 3 ) 2 C(CH 3 ) 2 O). 1 H NMR (400 MHz, CDCl 3 ) δ 7.38-7.21 (m, 5H, Ar-H), 5.24 (q, J = 6.5 Hz,1H, OCH), 1.49 (d, J = 6.5 Hz, 3H, CH 3 ), 1.22 (d, J = 11.9 Hz, 12H, CH 3 ). 13 CNMR (101 MHz, CDCl 3 ) δ 144.09 (Ar-C), 127.71 (Ar-C), 126.62 (Ar-C), 124.86(Ar-C), 82.26 (OC)...

Embodiment 2

[0029] Example 2: Lithium p-methylanilide catalyzes the hydroboration reaction of p-fluoroacetophenone and pinacol borane

[0030] In the reaction flask that has been dehydrated and deoxygenated, add 20ul of tetrahydrofuran solution (0.05M) of p-methylanilinide lithium under the protection of argon (0.1 mol% dosage), then add 0.1596 mL of borane with a syringe, mix well, and use 0.1208 mL of p-fluoroacetophenone was added into the syringe, and the mixture was stirred at room temperature. After 20 min of reaction, the NMR yield was 99%, and then a small amount of tetrahydrofuran and excess borane were removed under reduced pressure to obtain the corresponding pinacol boronic acid ester. 1 H NMR (400 MHz, CDCl 3 )δ 7.35-7.30 (m, 2H, Ar-H), 7.02-6.96 (m, 2H, Ar-H), 5.22 (q, J = 6.4 Hz, 1H,OCH), 1.47 (d, J = 6.5 Hz, 3H, CH 3 ), 1.22 (d, J = 11.6 Hz, 12H, CH 3 ). 13 C NMR (101 MHz, CDCl 3 ) δ 161.94 (ds, Ar-C), 140.34 (d, J = 3.1 Hz, Ar-C), 127.02(d, J = 8.0 Hz, Ar-C...

Embodiment 3

[0031] Example 3: Hydroboration reaction of m-fluoroacetophenone and pinacol borane catalyzed by p-methylanilide lithium

[0032] In the reaction flask that has been dehydrated and deoxygenated, add 20ul of tetrahydrofuran solution (0.05M) of p-methylanilinide lithium under the protection of argon (0.1 mol% dosage), then add 0.1596 mL of borane with a syringe, mix well, and use 0.1226 mL of m-fluoroacetophenone was added into the syringe, and the mixture was stirred at room temperature. After 20 min of reaction, the NMR yield was 99%. After that, a small amount of tetrahydrofuran and excess borane were removed under reduced pressure to obtain the corresponding pinacol boronic acid ester. 1 H NMR (400 MHz, CDCl 3 )δ 7.29-7.24 (m, 1H, Ar-H), 7.12-7.08 (m, 2H, Ar-H), 6.94-6.89 (m, 1H, Ar-H),5.23 (q, J = 6.4 Hz, 1H, OCH), 1.48 (d, J = 6.5 Hz, 3H, CH 3 ), 1.23 (d, J =11.4 Hz, 12H, CH 3 ). 13 C NMR (101 MHz, CDCl 3 ) δ 162.85 (ds, Ar-C), 147.26 (d, J = 6.9 Hz, Ar-C), 129...

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Abstract

The invention discloses a method for preparing borate by utilizing p-toluidine lithium. The method comprises the following steps: in a water-free and oxygen free environment and in an inert gas atmosphere, adding boron into a reaction bottle subjected to dehydration and deoxygenation treatment, then adding a catalyst (p-toluidine lithium), uniformly mixing, then adding ketone, carrying out hydroboration reaction, and carrying out termination reaction by being exposed to the air, so that borate is obtained, wherein the ketone is aromatic ketone or heterocyclic ketone. The invention firstly finds that p-toluidine lithium can catalyze the hydroboration reaction on the aromatic ketone or heterocyclic ketone and borane, and a new scheme is provided for preparation of borate by carrying out thehydroboration reaction on a carbonyl compound and borane.

Description

technical field [0001] The application of the p-toluide lithium involved in the present invention specifically relates to a method for preparing boric acid ester by using p-toluide lithium. technical background [0002] A variety of catalysts have been used for the hydroboration of ketones, and especially in recent years there have been numerous reports of such reactions. Due to the absence of catalysts, the hydroboration reaction of carbonyl compounds is difficult to occur. Therefore, the focus of research on this type of reaction is to develop efficient catalytic systems. The research on the hydroboration reaction of unsaturated bonds is of great significance to modern industry and organic synthesis chemistry, which has attracted extensive attention of scientific researchers. However, in the catalytic systems reported so far, the catalysts are relatively expensive, or the reaction conditions are relatively harsh. [0003] Therefore, it is particularly urgent to develop ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04B01J31/02
CPCB01J31/0252C07F5/04
Inventor 薛明强朱章野颜丹丹郑煜陈素芳沈琪
Owner SUZHOU UNIV
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