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Hydroboration reaction method for aldehyde ketone catalyzed by Grignard reagent

A Grignard reagent, a technology for catalyzing aldehydes and ketones, applied in the field of hydroboration reaction, can solve the problems of long yield, high temperature and the like, and achieve the effects of high yield, low toxicity and high reactivity

Active Publication Date: 2019-06-28
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this reaction system requires relatively high temperature and long time to obtain high yield
More importantly, this method is only applicable to aldehyde compounds, not suitable for sterically hindered ketone compounds [Stachowiak.H, J, K, Hreczycho. G, Green Chem.2018, 20, 1738-1742]

Method used

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  • Hydroboration reaction method for aldehyde ketone catalyzed by Grignard reagent
  • Hydroboration reaction method for aldehyde ketone catalyzed by Grignard reagent
  • Hydroboration reaction method for aldehyde ketone catalyzed by Grignard reagent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Methylmagnesium iodide catalyzes the reaction of benzaldehyde and pinacol borane, and the process is as follows:

[0016] In the glove box, sequentially add methylmagnesium iodide 0.05mol%, benzaldehyde 0.2mmol, pinacol borane 0.22mmol in the reaction bottle, then move it out of the glove box, stir for 10min, and obtain the productive rate by nuclear magnetic spectrum 99%. 1 H NMR (600MHz, CDCl 3 ): δ7.27-7.16 (m, 5H, Ar-H), 4.84 (s, 2H, OCH 2 ), 1.18(s, 12H, BOCMe 2 ). 13 C{ 1 H} NMR (151MHz, CDCl 3 ): δ139.45, 128.39, 127.47, 126.88 (Ar-C), 83.06 (BOCMe 2 ), 66.83 (OCH 2 ), 24.74 (BOCMe 2 ). 11 B{ 1 H} NMR (193MHz, CDCl 3 ): δ22.40.

[0017] The product structure is:

[0018]

Embodiment 2

[0020] Methylmagnesium bromide catalyzes the reaction of benzaldehyde and pinacol borane, and the process is as follows:

[0021] In the glove box, sequentially add methylmagnesium bromide 0.05mol%, benzaldehyde 0.2mmol, pinacol borane 0.22mmol in the reaction bottle, then move it out of the glove box, stir for 10min, and obtain the productive rate by nuclear magnetic spectrum 98%. 1 H NMR (600MHz, CDCl 3 ): δ7.27-7.16 (m, 5H, Ar-H), 4.84 (s, 2H, OCH 2 ), 1.18(s, 12H, BOCMe 2 ). 13 C{ 1 H} NMR (151MHz, CDCl 3 ): δ139.45, 128.39, 127.47, 126.88 (Ar-C), 83.06 (BOCMe 2 ), 66.83 (OCH 2 ), 24.74 (BOCMe 2 ). 11 B{ 1 H} NMR (193MHz, CDCl 3 ): δ22.40.

[0022] The product structure is:

[0023]

Embodiment 3

[0025]Methylmagnesium chloride catalyzes the reaction of benzaldehyde and pinacol borane, and the process is as follows:

[0026] In the glove box, 0.05mol% of methylmagnesium chloride, 0.2mmol of benzaldehyde, and 0.22mmol of pinacol borane were successively added to the reaction bottle, and then it was removed from the glove box, stirred for 10min, and the yield was 97% by nuclear magnetic spectrum . 1 H NMR (600MHz, CDCl 3 ): δ7.27-7.16 (m, 5H, Ar-H), 4.84 (s, 2H, OCH 2 ), 1.18(s, 12H, BOCMe 2 ). 13 C{ 1 H} NMR (151MHz, CDCl 3 ): δ139.45, 128.39, 127.47, 126.88 (Ar-C), 83.06 (BOCMe 2 ), 66.83 (OCH 2 ), 24.74 (BOCMe 2 ). 11 B{ 1 H} NMR (193MHz, CDCl 3 ): δ22.40.

[0027] The product structure is:

[0028]

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Abstract

The invention discloses a hydroboration reaction method for an aldehyde ketone catalyzed by a Grignard reagent and belongs to the technical field of hydroboration reactions. According to the method, the Grignard reagent is added into a mixture of an aldehyde or a ketone and pinacolborane under anhydrous anaerobic conditions, and the mixture above is stirred for a reaction at the room temperature.According to the hydroboration reaction method for the aldehyde ketone catalyzed by the Grignard reagent, the operation is simple, the use amount of the catalyst is low, the reaction activity is high,the expansion range of reactants is wide, and the yield is high.

Description

technical field [0001] The invention relates to the technical field of hydroboration reaction, in particular to a hydroboration reaction method of aldehydes and ketones catalyzed by Grignard reagents. Background technique [0002] In modern organic synthesis, it is necessary to use cheap and environmentally friendly catalysts for various organic transformations. In particular, earth-abundant and biocompatible main-group metals lack sufficient attention compared with noble metal-catalyzed organic reactions. Advocate the use of abundant, non-toxic and harmless metals, which is in line with the principles of green chemistry. Furthermore, the use of simple, readily available catalysts is still limited. In most cases, we use bulky ligands to synthesize metal compounds [Su.B, Cao.Z.C, Shi.Z.J, Acc.Chem.Res.2015, 48, 886-896; Liu.C, Zhang. Y, Qian.Q, Yuan.D, Yao.Y, Org.Lett.2014, 16, 6172-6175; Holzwarth.M.S, Plietker.B, ChemCatChem.2013, 5, 1650-1679]. Therefore, it is imperat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/04
Inventor 马猛涛王未凡姚薇薇
Owner NANJING FORESTRY UNIV
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