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Organic antimony compound bearing a nitrogen-bridged ligand and its preparation and application

A technology of compound and antimony ion, which is applied in the field of organic antimony ion compound and its preparation, can solve the problems of poor stability of organic antimony compound, less application of organic antimony compound, weak Lewis acid, etc., achieve high catalytic activity and selectivity, and novel structure , prepare simple effects

Inactive Publication Date: 2009-09-30
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, to date, organoantimony compounds have been rarely used as catalysts in organic synthesis
The reason may be that the poor stability of organoantimony compounds or / and Lewis acidity is too weak, hindering their application

Method used

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  • Organic antimony compound bearing a nitrogen-bridged ligand and its preparation and application
  • Organic antimony compound bearing a nitrogen-bridged ligand and its preparation and application
  • Organic antimony compound bearing a nitrogen-bridged ligand and its preparation and application

Examples

Experimental program
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Effect test

preparation example 1

[0034] In a 50mL one-necked flask, add 0.05mmol organic antimony ion compound (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

[0036] In a 50mL one-necked flask, add 0.05mmol organic antimony ion compound (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

[0038] In a 50mL one-necked flask, add 0.05mmol organic antimony ion compound (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 present invention discloses a new type of organic antimony compound bearing a nitrogen-bridged ligand. The structural formula of the ligand is [PhCH2]N[R][CH2Ph], wherein R is a substituent on nitrogen atom; group X that directly links antimony is an anion with strong charge pulling ability; and in this antimony compound, Sb<3+> not only forms bonds with the two carbon atoms of the ligand but also forms a coordinate bond with the nitrogen atom of the ligand and an ionic bond with the corresponding anion. The present invention also provides the preparation method of this organic antimony compound, as well as its application in organic synthesis as a catalyst.

Description

【Technical field】 [0001] The invention belongs to metal antimony ion compounds and their synthesis and application, in particular to a new type of organic antimony ion compounds containing bridging nitrogen atom ligands, their preparation method and catalytic application. 【Background technique】 [0002] Organometallic compounds containing organic groups or organic ligand structures have the advantages of easy modulation of reactivity or catalytic performance, and have attracted more and more attention of scholars. Antimony, as a main group metal element, belongs to group 15 in the periodic table of elements, and its compounds usually use three 6p electrons to form bonds and two 6s electrons as inert electron pairs, so trivalent antimony compounds are relatively common. However, so far, organoantimony compounds have been rarely used as catalysts in organic synthesis. The reason may be that the poor stability of organoantimony compounds or / and Lewis acidity is too weak, hinde...

Claims

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Application Information

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IPC IPC(8): C07F9/92B01J31/22C07C29/40C07C33/30
Inventor 尹双凤夏军邱仁华张晓文许新华陈浪
Owner HUNAN UNIV
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