A kind of Grignard reagent catalyzes the hydroboration reaction method of aldehyde and ketone

A technology of Grignard reagents and catalysis of aldehydes and ketones, which is applied in the field of hydroboration reaction, can solve the problems of long yield and high temperature, and achieve the effects of high yield, low toxicity and easy acquisition

Active Publication Date: 2021-06-25
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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  • A kind of Grignard reagent catalyzes the hydroboration reaction method of aldehyde and ketone
  • A kind of Grignard reagent catalyzes the hydroboration reaction method of aldehyde and ketone
  • A kind of Grignard reagent catalyzes the hydroboration reaction method of aldehyde and ketone

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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PUM

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Abstract

The invention discloses a hydroboration reaction method of aldehydes and ketones catalyzed by Grignard reagents, and belongs to the technical field of hydroboration reactions. The method is that the Grignard reagent is added to the mixture of aldehyde or ketone and pinacol borane under anhydrous and oxygen-free conditions, and the reaction is stirred at room temperature. The hydroboration reaction method of aldehydes and ketones catalyzed by the Grignard reagent of the present invention has the advantages of simple operation, small amount of catalyst, high reaction activity, wide expansion range of substrates and high yield.

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 Patents(China)
IPC IPC(8): C07F5/04
Inventor 马猛涛王未凡姚薇薇
Owner NANJING FORESTRY UNIV
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