Carborane-supported salen ligand, nested carborane-supported salen-Al catalyst and preparation and application thereof

A carborane and ligand technology, which is applied to carborane-supported salen ligands, nested carborane-supported salen-Al catalysts, and their preparation and application fields, achieving industrialization, a simple synthesis process, and high selectivity Effects of Sex and Yield

Active Publication Date: 2022-05-24
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] But so far, there is no report of Salen-Al compounds containing carborane. Carborane is a class

Method used

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  • Carborane-supported salen ligand, nested carborane-supported salen-Al catalyst and preparation and application thereof
  • Carborane-supported salen ligand, nested carborane-supported salen-Al catalyst and preparation and application thereof
  • Carborane-supported salen ligand, nested carborane-supported salen-Al catalyst and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0044] Example 1: Synthesis of Ligand L1

[0045] Diaminocarborane (1.85g) and salicylaldehyde (3.24g) were added to a 100ml round-bottomed flask, 60ml of toluene was added to dissolve it, and then 0.8ml of trifluoroacetic acid was added. The lower end of the branch port of the water separator, the other end of the water separator is connected to a reflux condenser, heated with an oil bath at 130 ° C until the reaction system refluxes, the oil bath is removed after the reaction for 6 hours, and the excess solvent is removed by rotary evaporation. The obtained black solid is recrystallized with ethanol and filtered to obtain Yellow solid (2.80 g, yield: 70%).

[0046]

[0047] 1HNMR (400.13MHz, CDCl3): δ11.15 (s, 2H, OH), 8.71 (s, 2H, N=CH), 7.47–7.42 (m, 4H, HPh), 7.03–6.96 (m, 4H, HPh) );

[0048] 13C{1H}NMR (100.61MHz, CDCl3): δ170.96(N=CH), 161.26(CPh), 135.57(CPh), 133.91(CPh), 119.92(CPh), 117.94(CPh), 117.81(CPh) ,93.43(Co-carb);

[0049] 11B{1H}NMR (160.46MHz, DM...

Example Embodiment

[0051] Example 2: Synthesis of Ligand L2

[0052]In a 100ml round-bottomed flask, add diaminocarborane (1.00g) and tripenta-di-tert-butylsalicylaldehyde (3.00g), add 60ml of toluene to dissolve, and then add 0.8ml of trifluoroacetic acid, The bottle mouth of the round-bottomed flask is connected to the lower end of the branch port of the water separator, and the other end of the water separator is connected to a reflux condenser, heated with an oil bath at 135 ° C until the reaction system refluxes, and the oil bath is removed after the reaction for 6 h, and the excess solvent is removed by rotary evaporation. Recrystallization from ethanol and filtration gave a yellow solid (2.70 g, yield: 77%).

[0053]

[0054] 1HNMR (400.13MHz, DMSO-d6): δ11.62(s, 2H, OH), 8.70(s, 2H, N=CH), 7.50(s, 2H, HPh), 7.20(s, 2H, HPh), 1.38(s,18H,tBu),1.32(s,18H,tBu);

[0055] 13C{1H}NMR (100.61MHz, CDCl3): δ171.72(N=CH), 158.66(CPh), 141.47(CPh), 137.72(CPh), 130.54(CPh), 128.14(CPh), 117.14(...

Example Embodiment

[0058] Example 3: Synthesis of Ligand L3

[0059] Diaminocarborane (2.37g) and tetramethoxysalicylaldehyde (4.76g) were added to a 100ml round-bottomed flask, 60ml of toluene was added to dissolve, and 0.8ml of trifluoroacetic acid was added. The mouth of the flask is connected to the lower end of the branch port of the water separator, and the other end of the water separator is connected to a reflux condenser, heated with an oil bath at 125 ° C until the reaction system refluxes, and the oil bath is removed after the reaction for 6 hours, and the excess solvent is removed by rotary evaporation. The obtained black solid is reconstituted with methanol. Crystallized and filtered to give a yellow solid (3.70 g, yield: 62%).

[0060]

[0061] 1HNMR (400.13MHz, DMSO-d6): δ11.55 (s, 2H, OH), 8.52 (s, 2H, N=CH), 7.22 (s, 2H, HPh), 6.49-6.44 (m, 4H, HPh) ),3.79(s,6H,OMe);

[0062] 13C{1H}NMR (100.61MHz, CDCl3): δ169.47(N=CH), 165.69(CPh), 163.81(CPh), 135.21(CPh), 111.89(CPh), 1...

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Abstract

The invention discloses a carborane supported salen ligand, a nested carborane supported salen-Al catalyst as well as preparation and application of the nested carborane supported salen ligand and the nested carborane supported salen-Al catalyst. The molecular structural formula of the carborane-supported salen ligand is shown in a formula I, and the molecular structural formula of the nested carborane-supported salen-Al complex is shown in a formula II. The preparation method comprises the following steps: reacting diamino-o-carborane with salicylaldehyde to obtain a salen ligand containing o-carborane; and then reacting with triethyl aluminum, so as to obtain the salen-Al complex containing the nested carborane. The method is simple in synthesis process and has good selectivity and yield.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals and monomer synthesis and catalytic application, and relates to a novel salen ligand and salen-Al complex, in particular to a carborane-supported salen ligand and a nested carborane-supported salen- Al catalyst and preparation method and application thereof, specifically a series of salen-Al complexes with different substituents on the benzene ring whose NN skeleton is nested carborane. Background technique [0002] Salen ligands are tetradentate Schiff base ligands containing [ONNO] produced by the reaction between diamine molecules and a specific class of aldehydes - salicylaldehyde. The salen ligands are easy to prepare, and the steric and electronic effects of the ligands can be modified by changing the bridging groups between NNs and the substituents on the salicylaldehyde benzene ring. At the same time, salen ligands can coordinate with many transition metals to generate salen metal ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07F5/06C07D317/36B01J31/22B01J31/02
CPCC07F5/027C07F5/069B01J31/2217B01J31/0239C07D317/36B01J2531/31Y02P20/584
Inventor 效旭琼康艳锐王贝宁南润霞黎译文朱周立
Owner HANGZHOU NORMAL UNIVERSITY
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