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Organic bismuth ion compound containing bridge nitrogen atom ligand, preparation and uses thereof

An ionic compound, organic bismuth technology, applied in the field of organic bismuth ionic compounds and its preparation, can solve the problems of catalyst effects, weak Lewis acidity, stability effects, etc., and achieve novel structure, high catalytic activity and selectivity, and simple preparation Effect

Inactive Publication Date: 2009-08-19
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are relatively few reports on the use of organobismuth compounds as catalysts
The reason may be that although some organic bismuth compounds are very stable, the Lewis acidity is too weak, and the effect as a catalyst is significantly affected.
At present, many scholars have reported that ionic organometallic Lewis acids have strong acidity, but their stability has been affected.

Method used

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  • Organic bismuth ion compound containing bridge nitrogen atom ligand, preparation and uses thereof
  • Organic bismuth ion compound containing bridge nitrogen atom ligand, preparation and uses thereof
  • Organic bismuth ion compound containing bridge nitrogen atom ligand, preparation and uses thereof

Examples

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Effect test

preparation example 1

[0035] Add 0.05mmol organic bismuth ion compound (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 = H, R' = Ph, X = OSO 2 C 8 f 17 ) and 1.0 mmol benzaldehyde, after stirring for 5 minutes, tetraallyl tin (0.3 mmol) was added, placed in a water bath reactor with magnetic stirring, and reacted at room temperature 25° C. for 3 hours. TLC followed the reaction until the reaction was complete. The reaction result is: 1-phenyl-3-ene-butanol, the yield is 95.0%, and the selectivity of 1-phenyl-3-ene-butanol is 100%.

preparation example 2

[0037] Add 0.05mmol organic bismuth ion compound (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 =H, R'=Cy, X=OSO 2 C 8 f 17 ) and 1.0 mmol benzaldehyde, after stirring for 5 minutes, tetraallyl tin (0.3 mmol) was added, placed in a water bath reactor with magnetic stirring, and reacted at room temperature 25° C. for 3 hours. TLC followed the reaction until the reaction was complete. The reaction result is: 1-phenyl-3-ene-butanol, the yield is 96.0%, and the selectivity of 1-phenyl-3-ene-butanol is 100%.

preparation example 3

[0039] Add 0.05mmol organic bismuth ion compound (R 1 , R 2 , R 3 , R 4 =CH 3 , R 5 , R 6 , R 7 , R 8 =H, R'=t-Bu, X=OSO 2 C 8 f 17 ) and 1.0 mmol benzaldehyde, after stirring for 5 minutes, tetraallyl tin (0.3 mmol) was added, placed in a water bath reactor with magnetic stirring, and reacted at room temperature 25° C. for 3 hours. TLC followed the reaction until the reaction was complete. The reaction result is: 1-phenyl-3-ene-butanol, the yield is 98.0%, and the selectivity of 1-phenyl-3-ene-butanol is 100%.

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Abstract

The invention discloses a novel organic bismuth ion compound containing bridged nitrogen atom ligand. The structural formula of the ligand is (R<1>)(R<2>)(R<3>)(R<4>)PhCH2N[R']CH2Ph(R<5>)(R<6>)(R<7>)(R<8>), wherein, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7> and R<8> are any same or different radicals on a benzene ring; R' is substituents on nitrogen atoms; radicals X directly connected with bismuth are anions with stronger electrolysis capacity; and in the bismuth compound, Bi<3+> forms bonds with two carbon atoms in the ligand, a coordination bond with N atoms in the ligand and an ionic bond with the corresponding anions. The invention also provides a preparation method of the organic bismuth ion compound and application thereof to organic synthesis as a catalyst.

Description

【Technical field】 [0001] The invention belongs to metal bismuth ion compounds and their synthesis and application, in particular to a new type of organic bismuth ion compounds containing bridging nitrogen atom ligands, their preparation method and catalytic application. 【Background technique】 [0002] Bismuth belongs to group 15 in the periodic table, is the most metallic element in this group, and is the heaviest stable element in the periodic table. Bismuth typically uses 3 6p electrons for bonding and 2 6s electrons as an inert electron pair. Therefore, most bismuth compounds exist in the +3-valent form, and there are also many +5-valent organic bismuth compounds. Bismuth compounds have green and safe characteristics such as low cost, easy handling, low toxicity and low radioactivity. [0003] Although bismuth is a relatively nontoxic green heavy metal, its use as a catalyst in organic synthesis has been limited until today. Since inorganic bismuth compounds such as bi...

Claims

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Application Information

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IPC IPC(8): C07F9/94B01J31/22C07C29/40C07C33/30
Inventor 尹双凤邱仁华张晓文许新华夏军陈浪
Owner HUNAN UNIV
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