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Hydroboration reaction method of carbonic ester

A carbonate and hydroboration technology, applied in the field of hydroboration reaction, can solve the problem of high activity, and achieve the effects of easy synthesis, high yield and reduced catalyst dosage

Inactive Publication Date: 2020-10-13
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Esters are not as active as aldehydes and ketones due to steric hindrance and electronic effects, and there are relatively few studies on the hydroboration reaction of esters

Method used

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  • Hydroboration reaction method of carbonic ester
  • Hydroboration reaction method of carbonic ester
  • Hydroboration reaction method of carbonic ester

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Synthetic example

[0021] In the present invention, the preparation method of the above-mentioned catalyst lithium complex comprises the following steps, mixing the small molecule organolithium solution with the ligand solution, and then reacting to obtain the catalyst lithium complex; the chemical structural formula of the ligand is as follows:

[0022] .

[0023] In the present invention, in the small molecule organic lithium solution, the small molecule organic lithium includes n-butyllithium, and the solvent is an alkyl solvent, such as hexane; in the ligand solution, the solvent is an ether solvent, such as tetrahydrofuran.

[0024] In the present invention, the molar ratio of the small molecule organolithium to the ligand is 4:1, which has never been reported in the synthesis and application of the β-ketimine anion ligand.

[0025] specific:

[0026] m-Phenyl bridged β-ketoimine ligand (L ph h 2 )Synthesis

[0027]

[0028] Add 150 ml of absolute ethanol, 10.8 g of m-phenylenediam...

Embodiment 1

[0036] Embodiment one: [L ph’ Li 4 (THF) 4 ] 2 Catalytic Reduction of Ethylene Carbonate and Pinacol Borane

[0037] Under an inert gas atmosphere, 5.84 mg (0.005 mmol) of the catalyst was added to the reaction flask after dehydration and deoxygenation treatment, ethylene carbonate (33.3 μL, 0.5 mmol), pinacol borane (239.4 μL ,1.65 mmol), THF (200 μL), at 60 o After reacting in C for 120 min, use mesitylene (69.6 μL, 0.5 mmol) as the internal standard, stir evenly, draw a drop into the NMR tube with a dropper, and add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 99%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ) δ 3.90 (s, 4H, OCH 2 ), 1.21 (s, 24H, OBpin).

Embodiment 2

[0042] Embodiment two: [L ph’ Li 4 (THF) 4}] 2 Catalytic Reduction of Propylene Carbonate and Pinacol Borane

[0043] Under an inert gas atmosphere, 5.84 mg of the catalyst was added to the dehydrated and deoxygenated reaction flask, and propylene carbonate (42.4 μL, 0.5 mmol) and pinacol borane (239.4 μL, 1.65 mmol) were sequentially added with a pipette gun. , THF (200 μL), at 60 o After reacting in C for 120 min, use mesitylene (69.6 μL, 0.5 mmol) as the internal standard, stir evenly, draw a drop into the NMR tube with a dropper, and add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 99%. NMR data of the product: 1 H NMR (400 MHz, CDCl 3 ) δ 4.28-4.20 (m, 1H, CH 3 CH), 3.71 (d, J = 5.6 Hz, 2H, OCH 2 ), 1.21 (s, 12H, OBpin), 1.20 (s, 12H, OBpin).

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Abstract

The invention relates to a hydroboration reaction method of carbonic ester, in particular to a hydroboration reaction method taking carbonic ester and borane as raw materials. As an important non-metallocene ligand, beta-ketimine is easy to synthesize; the charge and space effect of the beta-ketimine can be conveniently regulated and controlled through the change of substituents at the alpha position and the beta position, and the beta-ketimine can be coordinated with metal through various coordination modes, so that metal complexes with diversified structures are formed. The novel carbonic ester hydroboration reaction method provided by the invention has a wide substrate application range.

Description

technical field [0001] The invention relates to a hydroboration reaction, in particular to a hydroboration reaction method using carbonate and borane as raw materials. Background technique [0002] The hydroboration reaction of unsaturated compounds has always been a research hotspot for researchers. So far, a large number of literatures have reported the hydroboration reaction of carbonyl compounds. Esters are not as active as aldehydes and ketones due to steric hindrance and electronic effects, and there are relatively few studies on the hydroboration reaction of esters. Carbonates, as a class of esters, have also attracted attention for their hydroboration reactions. At present, the main group metal Mg catalysts, transition metal Mn complexes and rare earth metal complexes have been developed. In 2019, Walter's research group reported a manganese pincer complex [Mn(Ph 2 PCH 2 SiMe 2 ) 2 NH(CO) 2 Br] catalyzed carboxylic acids, carbonates and CO 2 Reduction reactio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04C07F1/02B01J31/22
CPCC07F5/04C07F1/005B01J31/2217B01J2531/11B01J2531/0238B01J2231/64
Inventor 薛明强周帅徐晓娟康子晗陈素芳朱章野
Owner SUZHOU UNIV
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