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Application of n-butyllithium in catalyzing cyanosilylation reaction of aldehyde and silane

A technology of n-butyllithium and silyl cyanosilane is applied in the application field of organolithium compounds, which can solve the problems such as the limited scope of substrate trial and the difficulty of catalyst synthesis, and achieve the effects of simple and controllable reaction process, easy acquisition and low cost.

Pending Publication Date: 2020-06-09
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there are relatively few reports on the cyanosilication of ketones catalyzed by main group metals, and the synthesis of existing catalysts is relatively difficult, and the range of substrate trials is limited.

Method used

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  • Application of n-butyllithium in catalyzing cyanosilylation reaction of aldehyde and silane
  • Application of n-butyllithium in catalyzing cyanosilylation reaction of aldehyde and silane
  • Application of n-butyllithium in catalyzing cyanosilylation reaction of aldehyde and silane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment one: n-BuLi catalyzes the reaction of benzaldehyde and TMSCN

[0029] Under an inert gas atmosphere, add benzaldehyde (101.6 μL, 1 mmol), trimethylsilyl cyanide (137.6 μL, 1.1 mmol) and finally add 0.1% catalyst n-BuLi (20 μL, 0.01 M in THF), react at rt for 30 min, pipette a drop into the NMR tube, 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 7.41 – 7.30 (m, 5H, ArH), 5.42 (s, 1H, CH), 0.16 (s, 9H, CH 3 ), figure 1 its NMR spectrum.

Embodiment 2

[0033] Embodiment two: n-BuLi catalyzes the reaction of benzaldehyde and TMSCN

[0034] Under an inert gas atmosphere, add benzaldehyde (101.6 μL, 1 mmol), trimethylsilyl cyanide (150.1 μL, 1.2 mmol) and finally add 0.1 % catalyst to the dehydrated and deoxygenated reaction flask with a pipette gun n-BuLi (20 μL, 0.01 M in THF), react at rt for 30 min, pipette a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 99%. The NMR data of the product are the same as in Example 1.

[0035] Comparative example:

[0036]Under an inert gas atmosphere, add benzaldehyde (101.6 μL, 1 mmol) and trimethylsilyl cyanide (150.1 μL, 1.2 mmol) sequentially to the dehydrated and deoxygenated reaction vial with a pipette gun, and react at rt for 30 min After that, use a dropper to draw a drop into the nuclear magnetic tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 11%.

Embodiment 3

[0037] Embodiment three: n-Butyllithium catalyzes the reaction of benzaldehyde and TMSCN

[0038] Under an inert gas atmosphere, add benzaldehyde (101.6 μL, 1 mmol), trimethylsilyl cyanide (125.1 μL, 1 mmol) and finally add 0.1% catalyst to the reaction vial after dehydration and deoxygenation n-BuLi (20 μL, 0.01 M in THF), react at rt for 30 min, pipette a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 93%. The NMR data of the product are the same as in Example 1.

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Abstract

The invention discloses an application of n-butyllithium in catalyzing cyanosilylation reaction of aldehyde and silane. The n-butyllithium has high catalytic activity, low catalyst dosage and good substrate application range, and after n-butyllithium, aldehyde and silane are mixed, cyanosilylation reaction is carried out to obtain a cyanohydrin compound. The n-butyllithium reagent disclosed by theinvention has the advantages of commercialization, easiness in obtaining, low cost, no solvent, environmental friendliness and the like, has a very good catalytic effect on aldehyde, and is wide in substrate application range. Commercial n-butyllithium can efficiently catalyze the cyanosilylation reaction of aldehyde by using a relatively low catalyst dosage.

Description

technical field [0001] The invention relates to the field of application of organolithium compounds, in particular to the application of commercialized n-butyllithium in catalyzing the cyanidation reaction of aldehyde and trimethylsilyl cyanide. Background technique [0002] Cyanosilylation is one of the most fundamental carbon-carbon bond formation reactions in organic chemistry. The generated cyanohydrins are valuable substrates and important intermediates in industry, because they can be further transformed into many valuable organic compounds, such as α-hydroxy acids, α-amino acids, β-amino alcohols, etc. Trimethylsilyl cyanide (TMSCN) is by far the most commonly used cyanation reagent, which can be converted to trimethylsilyl cyanohydrin. In recent years, chemists have developed various catalysts, which are used to catalyze the cyanosilication reaction of carbonyl compounds and TMSCN. The cyanosilylation of carbonyl compounds and TMSCN catalyzed by Ca and Ca has only ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18B01J31/12
CPCC07F7/1804C07F7/188B01J31/122
Inventor 薛明强王雨虹徐晓娟康子晗周帅
Owner SUZHOU UNIV
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