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Carboxylic acid deoxidation hydroboration method

A hydroboration and carboxylic acid technology, which is applied in the field of catalytic reaction of magnesium metal compounds, achieves the effects of mild conditions, low catalyst consumption, and expanded application range

Inactive Publication Date: 2018-12-07
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, many applications of these compounds are stoichiometric, such as the synthesis of corresponding novel amino monodentate monovalent magnesium metal compounds, etc. On the contrary, there are fewer examples of amino monodentate magnesium alkyl compounds used as catalysts.

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0024] Large sterically hindered aminomagnesium alkyl compounds catalyze the synthesis of boronate compounds from benzoic acid and borane:

[0025] Under anhydrous and oxygen-free conditions, under the protection of nitrogen, in a glove box, add 0.25 mmol of benzoic acid into a Schlenk reaction flask with a stirring bar, then add 1.0 mmol of pinacol borane and mix well, and finally add a catalyst with a large space 0.00025 mmol of magnesium alkyl compounds stabilized by hindered amino ligands, stirred and reacted at 60°C for 1 hour, briefly pumped under the vacuum pump, and added CDCl 3 Measure NMR. Calculated 1 H spectrum yield 99%. NMR data of the main product: 1 H NMR (600MHz, CDCl 3 ): δ1.25 (s-overlap, 36H, CH 3 , OBpin&pinBOBpin), 4.91(s, 2H, OCH 2 ), 7.23-7.34 (m, 5H, ArH).

Embodiment 2

[0027] Large sterically hindered aminomagnesium alkyl compound catalyzes the synthesis of boronate compounds from p-toluic acid and borane:

[0028] Under anhydrous and oxygen-free conditions, under nitrogen protection, in a glove box, add 0.25 mmol of p-toluic acid to a Schlenk reaction flask with a stirring bar, then add 1.0 mmol of pinacol borane and mix well, and finally add the catalyst 0.00025 mmol of magnesium alkyl compound stabilized by large sterically hindered amino ligands, stirred and reacted at 60°C for 1 hour, briefly pumped under vacuum pump, and added CDCl 3 Measure NMR. Calculated 1 H spectrum yield 98%. NMR data of the main product: 1 H NMR (600MHz, CDCl 3 ): δ1.25 (s-overlap, 36H, CH 3 , OBpin&pinBOBpin), 2.32(s, 3H, ArCH 3 ), 4.87 (s, 2H, OCH 2 ), 7.12(d, 3 J HH =7.8Hz, 2H, ArH), 7.22(d, 3 J HH = 7.8 Hz, 2H, ArH).

Embodiment 3

[0030] Large sterically hindered aminomagnesium alkyl compound catalyzes the synthesis of boronate compounds from p-tert-butylbenzoic acid and borane:

[0031] Under anhydrous and oxygen-free conditions, under nitrogen protection, in a glove box, add 0.25 mmol of p-tert-butylbenzoic acid to a Schlenk reaction flask with a stirring bar, then add 1.0 mmol of pinacol borane and mix well, and finally add Catalyst 0.00025 mmol of magnesium alkyl compound stabilized by large sterically hindered amino ligands, stirred and reacted at 60°C for 1 hour, briefly pumped under vacuum pump, and added CDCl 3 Measure NMR. Calculated 1 H spectrum yield 99%. NMR data of the main product: 1 H NMR (600MHz, CDCl 3 ): δ1.26 (s-overlap, 36H, CH 3 , OBpin&pinBOBpin), 1.31(s, 9H, C(CH 3 ) 3 ), 4.89 (s, 2H, OCH 2 ), 7.27(d, 3 J HH = 8.4 Hz, 2H, ArH), 7.35 (m, 2H, ArH).

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Abstract

The invention discloses a carboxylic acid deoxidation hydroboration method. The method comprises the following steps: adding carboxylic acid into a Schlenk reaction bottle under the protection of nitrogen in an anhydrous oxygen-free and reaction solvent-free condition; adding pinacolborane, and uniformly mixing; adding a high steric hindrance amino magnesium alkyl compound, and reacting to obtaina hydroborated product. The preparation method adopts a magnesium alkyl compound with stable high steric hindrance amino ligand to catalyze the reaction for synthesizing borate compounds from carboxylic acid and borane, has high catalytic activity, no solvent and simple structure, is easy to synthesize, can provide a new scheme for borate compound synthesis from carboxylic acid and borane and canwiden the application range of the magnesium alkyl compound with stable high steric hindrance amino ligand. The method has the advantages of a non-toxic reaction system, no solvent, mild condition, low catalyst dosage, simple reaction step and the like, and highly accords with the concept of environment-friendly chemistry.

Description

technical field [0001] The invention relates to the technical field of catalytic reactions of magnesium metal compounds, in particular to a magnesium alkyl compound stabilized by a large steric hindered amino ligand, a preparation method thereof and an application in carboxylic acid deoxyboration hydroboration. Background technique [0002] As an important class of boron compounds, organic borate compounds have great potential medical and synthetic value in the chemical industry, because of their good non-toxic, pollution-free, and good flame retardant, anti-wear and anti-corrosion properties. Combustibility has always been one of the key research topics for scientists. The organic borate derivatives synthesized by reduction of different organic group substrates expand the application range of organic borates. They usually have the characteristics of easy synthesis, high conversion rate, low cost, and good environmental adaptability. Therefore, boric acid esters can not onl...

Claims

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Application Information

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IPC IPC(8): C07F5/04
CPCC07F5/04
Inventor 马猛涛李佳罗曼肖钤
Owner NANJING FORESTRY UNIV
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