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Application of o-methoxyanilinolithium in Catalytic Hydroboration of Imines and Boranes

An o-methoxyaniline-based, catalytic imine technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve the problem of low yield of the catalytic system, Long reaction time, expensive catalyst and other problems, to achieve the effect of good universality, short reaction time, simple and controllable reaction

Active Publication Date: 2021-07-20
NANTONG TEXTILE & SILK IND TECH RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The hydroboration reaction of imines has become a research hotspot in recent years. The reported catalysts applied to the hydroboration reaction of imines mainly include the catalytic system of main group elements: magnesium [Manna, K.; Ji, P.; Greene, F. X. ; Lin, W. J.Am. Chem. Soc. 2016, 138, 7488−7491], calcium [Yadav, S.; Pahar, S.; Sen, S. S.Chem. Commun. 2017, 53 (33), 4562-4564], Sodium [Wu, Y.; Shan, C.; Ying, J.; Su, J.; Zhu, J.; Liu, L. L.; Zhao, Y. Green Chem. 2017, 19, 4169–4175]; however, currently In the reported catalytic systems, the catalysts are relatively expensive or difficult to prepare, or the reaction time is long and the reaction must be performed at high temperature, and the yield of some catalytic systems is very low

Method used

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  • Application of o-methoxyanilinolithium in Catalytic Hydroboration of Imines and Boranes
  • Application of o-methoxyanilinolithium in Catalytic Hydroboration of Imines and Boranes
  • Application of o-methoxyanilinolithium in Catalytic Hydroboration of Imines and Boranes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Lithium o-methoxyanilide catalyzes the hydroboration reaction of benzidine and pinacol borane

[0024] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of aniline under the protection of argon, add 100ul THF, then add 0.5 mmol (0.0726 mL) borane with a pipette and mix well, and finally add 39.2 ul of o-methoxy Tetrahydrofuran solution (0.6387M) of lithium anilide lithium (5 mol% dosage, the same below), after reacting for 2 h, draw a drop into the NMR tube with a dropper, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 91%. NMR data of the product: 1 H NMR (CDCl3, 400 MHz) δ: 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 1H), 1.29 (s, 12H).

Embodiment 2

[0025] Embodiment two: o-methoxyanilinolithium catalyzes the hydroboration reaction of benzidine and pinacol borane

[0026] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of aniline under argon protection, add 100ul THF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 39.2 ul of o-methoxy Lithium anilide tetrahydrofuran solution (0.6387M) (5 mol% dosage, the same below), after reacting for 1 h, use a dropper to draw a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 96%. NMR data of the product: 1 H NMR (CDCl 3 ,400MHz) δ : 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).

Embodiment 3

[0027] Example 3: Lithium o-methoxyanilide catalyzes the hydroboration reaction of benzidine and pinacol borane

[0028] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of aniline under argon protection, add 100ul THF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 39.2 ul of o-methoxy Tetrahydrofuran solution (0.6387M) (5 mol% dosage) of phenylanilinide lithium, after reacting for 2 h, draw a drop into the NMR tube with a dropper, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 99%. NMR data of the product: 1 H NMR (CDCl 3 , 400MHz) δ : 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).

[0029] Substitution of lithium o-methoxyanilinate by the lithium amide compound of formula I did not yield the product.

[0030]

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Abstract

The invention relates to the application of o-methoxyanilino lithium, in particular to the application of o-methoxyanilino lithium in catalyzing the hydroboration reaction of imine and borane. Stir and mix the catalyst, borane and imine in sequence, react for 1 to 2 hours, and expose to the air to terminate the reaction, remove the solvent from the reaction solution under reduced pressure, and obtain boric acid esters with different substituents. The o-methoxyanilinide lithium disclosed in the present invention can catalyze the hydroboration reaction of imine and borane with high activity at room temperature, and the amount of catalyst is only 4-5 mol% of the molar weight of imine, and the reaction can reach 90% The above yield, compared with the existing catalytic system, utilizes simple o-methoxyanilinide lithium, the reaction conditions are mild, and the yield of borate esters with different substituents can reach 99% under optimized conditions.

Description

technical field [0001] The application of the o-methoxyanilinolithium involved in the present invention specifically relates to the efficient application of the o-methoxyanilinolithium in catalyzing the hydroboration reaction of imine and borane. [0002] technical background [0003] Amine compounds and their derivatives are ubiquitous in nature, especially in the biological world, and have extremely important physiological functions. They are important organic compounds in the fields of biology, chemistry, medicine, etc. Many drugs contain amine functional groups, namely amino groups, such as amino groups in proteins, nucleic acids, antibiotics and alkaloids. Amine compounds have many uses and a wide range of applications. They are often used in the synthesis of textiles, dyes, polymers, pigments and pesticides. Since the hydroboration reaction of carbonyl groups is much easier than that of amines, the development of an efficient catalytic system for the hydroboration reac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02B01J31/02
CPCB01J31/0252C07F5/022
Inventor 薛明强颜丹丹郑煜蔡玲霞刘倩倩沈琪
Owner NANTONG TEXTILE & SILK IND TECH RES INST
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