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Organic bismuth ion compound containing bridge nitrogen atom ligand, preparation and uses thereof
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An ionic compound and organic bismuth technology, applied in the field of organic bismuth ionic compounds and their preparation, can solve the problems of weak Lewis acidity, influence of catalyst effect, influence of stability and the like, and achieve high catalytic activity and selectivity, novel structure and simple preparation. Effect
Inactive Publication Date: 2014-04-09
HUNAN UNIV
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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.
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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...
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