Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing borate on basis of lithium o-toluidine

An o-toluidine-based, 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 catalysts. Expensive, harsh reaction conditions and other problems, to achieve the effect of good universality, short reaction time and high catalytic activity

Inactive Publication Date: 2018-08-24
SUZHOU UNIV
View PDF1 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing borate on basis of lithium o-toluidine
  • Method for preparing borate on basis of lithium o-toluidine
  • Method for preparing borate on basis of lithium o-toluidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Hydroboration reaction of acetophenone and pinacol borane catalyzed by o-methylanilide lithium

[0029] In the reaction flask that has been dehydrated and deoxygenated, add 40ul of tetrahydrofuran solution (0.05M) (0.2 mol% dosage) of o-toluidine lithium under the protection of argon, 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), 72.10 (...

Embodiment 2

[0030] Example 2: Lithium o-methylanilide catalyzes hydroboration reaction of p-fluoroacetophenone and pinacol borane

[0031] In the reaction flask that has been dehydrated and deoxygenated, add 40ul of tetrahydrofuran solution (0.05M) (0.2 mol% dosage) of o-toluidine lithium under the protection of argon, then add 0.1596 mL of borane with a syringe, mix well, and then 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), 11...

Embodiment 3

[0032] Example 3: Hydroboration reaction of m-fluoroacetophenone and pinacol borane catalyzed by o-methylanilide lithium

[0033] In the reaction flask that has been dehydrated and deoxygenated, add 40ul of tetrahydrofuran solution (0.05M) (0.2 mol% dosage) of o-toluidine lithium under the protection of argon, then add 0.1596 mL of borane with a syringe, mix well, and then 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%, 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 7.29-7.24 (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), 129.67 ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing borate on basis of lithium o-toluidine. Borane is added to a reaction bottle subjected to dehydration and deoxidation treatment in a water-free and oxygen-free environment in an inert gas atmosphere, then, a lithium o-toluidine catalyst is added, the mixture is uniformly mixed, ketone is added, a hydroboration reaction is conducted, the reaction is ended by exposing the mixture to the air, and borate is obtained. The ketone is aromatic ketone or heterocyclic ketone. It is found for the first time that lithium o-toluidine can extremely efficientlycatalyze the hydroboration reaction of aromatic ketone or heterocyclic ketone with borane, and a new scheme is provided for preparing borate through the hydroboration reaction of a carbonyl compound and borane.

Description

technical field [0001] The application of the o-toluidelithium involved in the present invention specifically relates to a method for preparing boric acid ester based on o-toluidelithium. technical background [0002] 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. [0003] 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. However, in the catalytic systems reported so far, the catalysts are relatively expensive, or the reaction conditions are relatively harsh. [0004] Therefore, it is particularly urgent to d...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07F5/02B01J31/02
CPCC07F5/025B01J31/0252
Inventor 薛明强朱章野武振杰洪玉标蔡玲霞沈琪
Owner SUZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com