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Rare earth complex based on diimine ligands and application of rare earth complex

A diimine ligand, rare earth metal technology, applied in the field of chemistry, can solve the problem of inability to catalyze tertiary aromatic amines, etc., and achieve the effect of wide application range of substrates, excellent chemical selectivity and regioselectivity

Active Publication Date: 2017-11-03
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, this kind of reaction mainly adopts subgroup IV and V catalysts, and the substrates must be primary or secondary amines, and cannot catalyze the reaction of tertiary aromatic amines.

Method used

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  • Rare earth complex based on diimine ligands and application of rare earth complex
  • Rare earth complex based on diimine ligands and application of rare earth complex
  • Rare earth complex based on diimine ligands and application of rare earth complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

[0043] Weigh L1 (35mg), [PhNHMe 2 ][B(C 6 f 5 ) 4 ] (38mg), dissolved in toluene, reacted at room temperature for 8 hours. After the reaction was complete, N,N-dimethylaniline (86 mg) and 1-hexene (40 mg) were added and heated at 120° C. for 10 hours. After the reaction was completed, the toluene was drained to obtain an oily residue, which was separated by column chromatography to obtain a light yellow oily liquid (89 mg, 91% yield).

[0044] HRMS (ESI) m / z calculated value: For C 14 h 23 N[M+H] + :206.1903; Measured value: 206.1909.

[0045] 1 H NMR (400MHz,C 6 D. 6 ,298K):δ=7.26(m,2H,m-Ph),6.78(m,1H,p-Ph),6.68(m,2H,o-Ph),3.00(dd, 2 J HH =14.5Hz, 3 J HH =6.6Hz,1H,CH 2 N),2.80(dd, 2 J HH =14.5Hz, 3 J HH =8.1Hz,1H,CH 2 N),2.63(s,3H,CH 3 N),1.78(m,1H,CHCH 3 ),1.23(m,1H,CHCH 2 ),1.23(m,1H,CH 2 ),1.23(m,2H,CH 2 CH 3 ),1.10(m,1H,CH 2 ),0.93(m,1H,CHCH 2 ),0.87(t, 3 J HH =6.9Hz,3H,CH 2 CH 3 ),0.77(d, 3 J HH =6.7Hz,3H,CHCH 3 ).

[0046]...

Embodiment 2

[0048]

[0049] Weigh L1 (35mg), [PhNHMe 2 ][B(C 6 f 5 ) 4 ] (38mg), dissolved in toluene, reacted at room temperature for 8 hours. After the reaction was complete, N,N-dimethylaniline (86 mg) and 1-decene (67 mg) were added and heated at 120° C. for 22 hours. After the reaction was completed, the toluene was drained to obtain an oily residue, which was separated by column chromatography to obtain a light yellow oily liquid (100 mg, 80% yield).

[0050] HRMS (ESI) m / z calculated value: For C 18 h 31 N[M+H] + :262.2529; Measured value: 262.2536.

[0051] 1 H NMR (400MHz,C 6 D. 6 ,298K): δ=7.26(m,2H,m-Ph),6.78(m,1H,p-Ph),6.69(m,2H,o-Ph),3.02(dd, 2 J HH =14.5Hz, 3 J HH =6.7Hz,1H,CH 2 N),2.82(dd, 2 J HH =14.5Hz, 3 J HH =8.0Hz,1H,CH 2 N),2.64(s,3H,CH 3 N),1.82(m,1H,CHCH 3 ),1.27(m,13H,CH 2 ),0.99(m,1H,CHCH 2 ),0.92(t, 3 J HH =6.8Hz,3H,CH 2 CH 3 ),0.79(d, 3 J HH =6.7Hz,3H,CHCH 3 ).

[0052] 13 C{ 1 H}NMR (101MHz,C 6 D. 6 ,298K): δ=150.2(i-Ph), 1...

Embodiment 3

[0054]

[0055] Weigh L1 (35mg), [PhNHMe 2 ][B(C 6 f 5 ) 4 ] (38mg), dissolved in toluene, reacted at room temperature for 8 hours. After the reaction was complete, N,N-dimethylaniline (86 mg) and allyltrimethylsilane (54 mg) were added and heated at 120° C. for 8 hours. After the reaction was completed, the toluene was drained to obtain an oily residue, which was separated by column chromatography to obtain a light yellow oily liquid (101 mg, 90% yield).

[0056] HRMS (ESI) m / z calculated value: For C 14 h 25 NSi[M+H] + :236.1829; Measured value: 236.1837.

[0057] 1 H NMR (400MHz,C 6 D. 6 ,298K):δ=7.26(m,2H,m-Ph),6.78(m,1H,p-Ph),6.70(m,2H,o-Ph),3.00(dd, 2 J HH =14.3Hz, 3 J HH =6.3Hz,1H,CH 2 N),2.80(dd, 2 J HH =14.3Hz, 3 J HH =8.5Hz,1H,CH 2 N),2.64(s,3H,CH 3 N),1.98(m,1H,CHCH 3 ),0.83(d, 3 J HH =6.6Hz,3H,CHCH 3 ),0.56(dd, 2 J HH =14.6Hz, 4 J HH =4.0Hz,1H,CH 2 SiMe 3 ),0.21(dd, 2 J HH =14.6Hz, 4 J HH =9.8Hz,1H,CH 2 SiMe 3 ),-0.01(s,9H,Si...

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PUM

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Abstract

The invention belongs to the technical field of organic synthesis. A catalyst is a rare earth complex based on diimine ligands. The invention further provides application of the rare earth catalyst in aromatic amine hydroamination and alkylation reaction.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and specifically relates to the use of a catalyst, in particular to the application of a rare earth metal catalyst in the alkylation reaction of aromatic amine hydroamine. Background technique [0002] Aromatic amines are widely found in natural products, medicines, and fine chemicals, and are a very important class of compounds. Aromatic amines with complex structures can be efficiently constructed through the hydroamine alkylation reaction of simple aromatic amines and alkenes. Since this is a 100% atom-economical reaction, it has attracted great attention. At present, this type of reaction mainly adopts subgroup IV and V catalysts, and the substrates must be primary or secondary amines, and cannot catalyze the reaction of tertiary aromatic amines. Contents of the invention [0003] The technical problem to be solved by the present invention is to efficiently catalyze the hydroamine alkyla...

Claims

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Application Information

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IPC IPC(8): C07F9/50B01J31/24C07C209/60C07C211/48C07C211/60C07C211/58C07F7/08
CPCB01J31/2404B01J2531/0244B01J2531/35C07C209/60C07F7/081C07F7/083C07F9/5045C07C211/48C07C211/60C07C211/58
Inventor 徐信高红杰苏健洪
Owner SUZHOU UNIV
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