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Application of beta-diimine divalent rare earth boron hydrogen complex to hydroboration of catalytic aldehyde and borane

A technology of β-diimine divalent rare earth and -diimine divalent rare earth is applied in the field of catalytic reaction of rare earth metal complexes to achieve high yield, high reaction efficiency and easy post-processing of products

Active Publication Date: 2016-10-26
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In modern organic chemistry of rare earth metals, self-assembled rare earth metal complexes have become a class of highly active catalytic systems due to ligands with unique structures and highly efficient and controllable initiator groups. The report of complexes catalyzing the hydroboration reaction of borane and carbonyl compounds. In view of the high catalytic effect of this type of complexes, expanding the application of this type of complexes is not only of great application value, but also of great importance to the research of organoboron chemistry. theoretical significance

Method used

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  • Application of beta-diimine divalent rare earth boron hydrogen complex to hydroboration of catalytic aldehyde and borane
  • Application of beta-diimine divalent rare earth boron hydrogen complex to hydroboration of catalytic aldehyde and borane
  • Application of beta-diimine divalent rare earth boron hydrogen complex to hydroboration of catalytic aldehyde and borane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment one: [2,6- i pr 2 -(C 6 h 3 )-NC(Me)CHC(Me)N-(C 6 h 3 )-2,6- i pr 2 ] Yb-BH 4 . 2THF Catalyzed Hydroboration of Benzaldehyde and Pinacol Borane

[0031] Add 0.1 mL of catalyst [2,6- i pr 2 -(C 6 h 3 )-NC(Me)CHC(Me)N-(C 6 h 3 )-2,6- i pr 2 ]Yb-BH 4 . 2THF in toluene (0.01 M), then add pinacol borane (0.145 mL, 1 mmol) by syringe, and then add benzaldehyde (0.101 mL, 1 mmol) by syringe. After reacting for 15 min, add 0.5 mL CDCl 3 , the NMR yield was 99%, and then the CDCl was dried under reduced pressure 3 and toluene mixed solution, add n-hexane (3 × 2 mL), and drain to obtain the corresponding pinacol borate, C 6 h 5 CH 2 OB(OC(CH 3 ) 2 C(CH 3 ) 2 O). NMR data of the product:

[0032] 1 H NMR (400 MHz, CDCl 3 ): 7.35−7.29 (m, 4H, ArH ), 7.27−7.22 (m, 1H, Ar H ), 4.92 (s, 2H, ArC H ), 1.25 (s, 12H, C(C H 3 ) 2 ) ppm. 11 B NMR (128 MHz, CDCl 3 ): 25.9 ppm.

Embodiment 2

[0033] Embodiment two: [2,6- i pr 2 -(C 6 h 3 )-NC(Me)CHC(Me)N-(C 6 h 3 )-2,6- i pr 2 ] Sm-BH 4 . 2THF Catalyzed Hydroboration of Benzaldehyde and Pinacol Borane

[0034] Add 0.01 mL of catalyst [2,6- i pr 2 -(C 6 h 3 )-NC(Me)CHC(Me)N-(C 6 h 3 )-2,6- i pr 2 ]Sm-BH 4 . 2THF in toluene (0.01 M), then 0.09 mL of toluene was added by syringe, then pinacol borane (0.145 mL, 1 mmol) was added by syringe, and benzaldehyde (0.101 mL, 1 mmol) was added by syringe, reaction 15 After min, add 0.5 mL CDCl 3 , the NMR yield was 90%, and then the CDCl was dried under reduced pressure 3 and toluene mixed solution, and to remove unreacted aldehyde, add n-hexane (3 × 2 mL), and drain to obtain the corresponding pinacol borate, C 6 h 5 CH 2 OB(OC(CH 3 ) 2 C(CH 3 ) 2 O). The NMR data of the product are the same as in Example 1.

Embodiment 3

[0035] Embodiment three: [2,6- i pr 2 -(C 6 h 3 )-NC(Me)CHC(Me)N-(C 6 h 3 )-2,6- i pr 2 ] Sm-BH 4 . 2THF Catalyzed Hydroboration of Benzaldehyde and Pinacol Borane

[0036] Add 0.05 mL of catalyst [2,6- i pr 2 -(C 6 h 3 )-NC(Me)CHC(Me)N-(C 6 h 3 )-2,6- i pr 2 ]Sm-BH 4 . 2 THF in toluene (0.01 M), then 0.05 mL of toluene was added by syringe, then pinacol borane (0.145 mL, 1 mmol) was added by syringe, and benzaldehyde (0.101 mL, 1 mmol) was added by syringe. After reacting for 10 min, add 0.5 mL CDCl 3 , the NMR yield was 94%, and then the CDCl was dried under reduced pressure 3 Mixed solution with toluene and remove unreacted aldehyde, add n-hexane (3 × 2 mL), and drain to obtain the corresponding pinacol borate, C 6 h 5 CH 2 OB(OC(CH 3 ) 2 C(CH 3 ) 2 O). The NMR data of the product are the same as in Example 1.

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Abstract

The invention discloses application of a beta-diimine divalent rare earth boron hydrogen complex to hydroboration of catalytic aldehyde and borane. The beta-diimine rare earth dichloride and NaBH4 react in a tetrahydrofuran solvent and then in-situ Na / K is utilized to reduce, so that the beta-diimine divalent rare earth boron hydrogen complex: [2,6-ipr2-(C6H3)-NC(Me)CHC(Me)N-(C6H3)-2,6-ipr2]Ln-BH4.2THF is acquired. The beta-diimine divalent rare earth boron hydrogen complex disclosed by the invention can high-actively catalyze the hydroboration of borane and aldehyde under a mild condition; the reaction time is short; the reaction condition is mild; the post-processing method is simple and convenient.

Description

technical field [0001] The invention relates to a catalytic reaction of a rare earth metal complex, in particular to the application of a β-diimine divalent rare earth borohydride complex in catalyzing the hydroboration reaction of borane and aldehyde. Background technique [0002] Organic borates are widely used in industrial production because of their stability and non-toxicity. They are an important class of industrial raw materials. Early borates were mainly used as plasticizers and welding fluxes. In the late 20th century, the application of boric acid esters developed rapidly, such as trimethyl borate, which was widely used in the preparation of high-energy fuels. In addition, it is also used as anti-friction and anti-friction additives for lubricating oils, rubber-metal adhesion promoters, stabilizers in polymers, etc. Organic borates are also a very important synthetic raw material in organic synthesis. Therefore, the synthesis of organic borates has always been ...

Claims

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Application Information

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IPC IPC(8): B01J31/22C07F5/04
CPCB01J31/2208C07F5/04
Inventor 薛明强洪玉标陈素芳沈琪
Owner SUZHOU UNIV
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