Schiff base rare earth ytterbium iodide, and preparation method and application thereof

A technology of iodide and Schiff base is applied in the field of metal organic compound preparation to achieve the effects of low toxicity, easy purification and high yield.

Inactive Publication Date: 2017-12-22
NANJING FORESTRY UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Schiff base heavy rare earth metal compounds and their catalytic hydroboration of aldehydes and ketones have not been reported so far

Method used

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  • Schiff base rare earth ytterbium iodide, and preparation method and application thereof
  • Schiff base rare earth ytterbium iodide, and preparation method and application thereof
  • Schiff base rare earth ytterbium iodide, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The preparation of N-(4-isopropyl-2,6-di(benzhydryl)phenyl)-3,5-di-tert-butyl-2-oxo-Schiff base rare earth ytterbium iodide is as follows:

[0023] In the absence of water and oxygen, in a single-port reaction tube, N-(4-isopropyl-2,6-bis(benzhydryl)phenyl)-3,5-di-tert-butyl-2-hydroxybenzaldehyde Dissolve imine 1.46mmol in 40mL tetrahydrofuran solution at -80°C, dissolve potassium hydride 1.46mmol in 5mL tetrahydrofuran and add dropwise, react at room temperature for 2h, dissolve ytterbium triiodide 1.46mmol in 20mL tetrahydrofuran, add dropwise at -80°C The above solution was reacted for 10 h, the solvent was drained, added to 40 mL of toluene for extraction, and concentrated to 10 mL. After a few days, yellow crystals were obtained. After filtration, the mass was 0.82 g, and the yield was 60%. M.p. 282-284°C. Elemental Analysis: C 100 h 104 IN 2 o 2 Yb: C, 72.10; H, 6.29; N, 1.68. Found C, 72.58; H, 6.63; N, 1.32. Infrared: IR(KBr,cm -1 ):3429,3061,3028,2960,28...

Embodiment 2

[0025] The preparation of N-(4-isopropyl-2,6-di(benzhydryl)phenyl)-3,5-di-tert-butyl-2-oxo-Schiff base rare earth ytterbium iodide is as follows:

[0026] In the absence of water and oxygen, in a single-port reaction tube, N-(4-isopropyl-2,6-bis(benzhydryl)phenyl)-3,5-di-tert-butyl-2-hydroxybenzaldehyde Dissolve imine 1.75mmol in 40mL tetrahydrofuran solution at -60°C, dissolve potassium hydride 2.10mmol in 5mL tetrahydrofuran and add dropwise, react at room temperature for 3h, dissolve ytterbium triiodide 1.75mmol in 20mL tetrahydrofuran, add dropwise at -60°C The above solution was reacted for 15 hours, the solvent was drained, added to 40 mL of toluene for extraction, and concentrated to 10 mL. After a few days, yellow crystals were obtained. After filtration, the mass was 0.98 g, and the yield was 59%. M.p. 282-284°C. Elemental Analysis: C 100 h 104 IN 2 o 2 Yb: C, 72.10; H, 6.29; N, 1.68. Found C, 72.58; H, 6.63; N, 1.32. Infrared: IR (KBr, cm -1):3429,3061,3028,296...

Embodiment 3

[0028] The preparation of N-(4-isopropyl-2,6-di(benzhydryl)phenyl)-3,5-di-tert-butyl-2-oxo-Schiff base rare earth ytterbium iodide is as follows:

[0029] In the absence of water and oxygen, in a single-port reaction tube, N-(4-isopropyl-2,6-bis(benzhydryl)phenyl)-3,5-di-tert-butyl-2-hydroxybenzaldehyde Dissolve imine 1.75mmol in 40mL tetrahydrofuran solution at -40°C, dissolve potassium hydride 2.10mmol in 5mL tetrahydrofuran and add dropwise, react at room temperature for 4h, dissolve ytterbium triiodide 1.75mmol in 20mL tetrahydrofuran, add dropwise at -40°C The above solution was reacted for 20 hours, the solvent was drained, added to 40 mL of toluene for extraction, and concentrated to 10 mL. After a few days, yellow crystals were obtained, filtered, and the mass was 0.99 g, with a yield of 61%. M.p. 282-284°C. Elemental Analysis: C 100 h 104 IN 2 o 2 Yb: C, 72.10; H, 6.29; N, 1.68. Found C, 72.58; H, 6.63; N, 1.32. Infrared: IR (KBr, cm -1 ):3429,3061,3028,2960,286...

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Abstract

The invention discloses Schiff base rare earth ytterbium iodide, and a preparation method and the application thereof. The Schiff base rare earth ytterbium iodide is N-(4-isopropyl-2,6-di(diphenylmethyl)phenyl)-3,5-ditert-butyl-2-oxygen Schiff base rare earth ytterbium iodide. The preparation method comprises the following steps: performing reaction on N-(4-isopropyl-2,6-di(diphenylmethyl)phenyl)-3,5-ditert-butyl-2-hydroxybenzaldimine and potassium hydride to obtain corresponding potassium salt under the conditions of no water and no oxygen, and performing reaction on the potassium salt and ytterbium iodide to obtain a yellow crystal, namely the N-(4-isopropyl-2,6-di(diphenylmethyl)phenyl)-3,5-ditert-butyl-2-oxygen Schiff base rare earth ytterbium iodide. The Schiff base rare earth ytterbium iodide is simple in synthesis, convenient in separation and purification, definite in structure and high in yield; the Schiff base rare earth ytterbium iodide serving as a catalyst has high activity of catalyzing reaction of aldehyde or ketone and pinacolborane and wide substrate universality.

Description

technical field [0001] The invention relates to the technical field of metal organic compound preparation, in particular to a Schiff base rare earth ytterbium iodide and its preparation and application. Background technique [0002] The hydroboration reaction is a reaction in which the hydrogen on the boron reagent is transferred to the unsaturated organic compound to form different organoboron compounds. The hydroboration reaction is widely used in the production of fine chemicals, the synthesis of materials, and the preparation of macromolecular composite materials. One of the most important reactions in the hydroboration reaction is the hydroboration of carbonyl compounds. Hydroboration is usually the equimolar addition of borane reagents to carbonyl compounds to form borates, which are then readily hydrolyzed to alcohols [Chong.C.C, Kinjo.R, ACS Catal.2015, 5, 3238-3259; Geier.S.J , Vogels. C.M, Westcott. S.A, ACSSymp. Ser. 2016, 1236, 209-225]. Due to the advantages ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/00B01J31/22C07C29/14C07C29/143C07C33/20C07C33/22C07C33/24C07C33/32C07C33/34C07C33/48C07C31/135C07C35/08C07C33/18C07C33/46C07C41/26C07C43/23C07C201/12C07C205/19C07C213/00C07C215/68C07C253/30C07C255/53C07D333/16
CPCB01J31/2217C07B2200/13C07C29/14C07C29/143C07C41/26C07C201/12C07C213/00C07C253/30C07D333/16C07F5/003C07C33/20C07C33/22C07C33/24C07C33/32C07C33/34C07C33/48C07C31/135C07C35/08C07C33/18C07C33/46C07C43/23C07C205/19C07C215/68C07C255/53B01J31/2243B01J2231/344B01J2231/64B01J2531/0252B01J2531/38C07C37/002C07C251/24C07C2601/14C07C2603/24C07C33/14C07C39/11
Inventor 马猛涛王未凡姚薇薇徐莉
Owner NANJING FORESTRY UNIV
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