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Synthesis method of borate

A synthesis method and borate ester technology are applied in the field of rare earth metal complex catalytic reaction, and achieve the effects of high yield, high reaction efficiency and easy product post-processing

Active Publication Date: 2018-06-15
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0007] 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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  • Synthesis method of borate

Examples

Experimental program
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Embodiment 1

[0031] 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

[0032] 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:

[0033] 1 H NMR (400 MHz, CDCl 3 ): 7.35−7.29 (m, 4H, Ar H ), 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 ): 25.9ppm.

Embodiment 2

[0034] 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

[0035] 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 add 0.09 mL of toluene by syringe, then add pinacol borane (0.145 mL, 1 mmol) by syringe, and then add benzaldehyde (0.101 mL, 1 mmol) 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

[0036] 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

[0037] 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 pinacolborane (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 a synthesis method of borate, which comprises the steps of allowing beta-diimido rare-earth dichloride and NaBH4 to give a reaction in a tetrahydrofuran solvent, and performingin-situ Na / K reduction to form a beta-diimido divalent rare-earth borohydride complex: [2,6-ipr2-(C6H3)-NC(Me)CHC(Me)N-(C6H3)-2,6-ipr2]Ln-BH4.2THF. The beta-diimido divalent rare-earth borohydride complex can highly actively catalyze hydroboration reaction of borane and aldehyde to synthesize borate under a mild condition; the reaction time is short; a reaction condition is mild; and a post-treatment method is simple and convenient.

Description

[0001] The present invention is the application of the β-diimine divalent rare earth borohydride complex in catalyzing the hydroboration reaction of aldehydes and boranes. The application date is June 30, 2016, and the application number is 201610502171.3. The case application is part of the preparation technology of the compound. technical field [0002] The invention relates to a catalytic reaction of a rare earth metal complex, in particular to a method for synthesizing a boric acid ester. Background technique [0003] 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-frictio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04
CPCB01J31/2208C07F5/04
Inventor 薛明强洪玉标陈素芳沈琪
Owner SUZHOU UNIV
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