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A kind of β-diimine monovalent magnesium compound and its preparation method and application in hydroboration of aldehydes and ketones

A technology of magnesium compound and diimine, applied in the field of metal organic compound preparation, can solve the problem that the application of the catalytic amount of monovalent magnesium compound is not reported, and achieve the effects of simple and easy operation of the reaction process, easy product and low toxicity of the article.

Active Publication Date: 2019-09-03
厦门欧瑞捷生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The application of the existing reported monovalent magnesium compound is stoichiometric, but the application of the catalytic amount of the monovalent magnesium compound has not yet been reported.

Method used

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  • A kind of β-diimine monovalent magnesium compound and its preparation method and application in hydroboration of aldehydes and ketones
  • A kind of β-diimine monovalent magnesium compound and its preparation method and application in hydroboration of aldehydes and ketones
  • A kind of β-diimine monovalent magnesium compound and its preparation method and application in hydroboration of aldehydes and ketones

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Experimental program
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Effect test

Embodiment 1

[0024] The preparation of the iodide of β-diimine magnesium, the process is as follows:

[0025] In the absence of water and oxygen, 3.27 mmol of β-diimine ligand was dissolved in 25 mL of ether solution in a single-port reaction tube, and 3.92 mmol of methylmagnesium iodide was added dropwise to the above solution at -80°C, and reacted at room temperature for 24 hours. After filtration, the solid was sucked dry, and the filtrate was concentrated to 5 mL to obtain colorless crystals. The mass of solid and crystals was 1.63 g, and the yield was 94%. M.p. 271-273°C. NMR spectrum: 1 HNMR (600MHz, C 6 D. 6 ):δ6.99-6.91(m,6H,Ar-H),4.88(s,1H,CH),3.12(s,4H,OCH 2 CH 3 ),2.65(s,6H,CH 3 ),2.08(s,6H,CH 3 ),1.55(s,6H,NCCH 3 ),0.48(s,6H,OCH 2 CH 3 ) ppm. 13 C{ 1 H}NMR (151MHz, C 6 D. 6 ):δ168.87 (NCCH 3 ), 147.75, 131.57, 129.56, 124.76 (Ar-C), 95.31 (=CH), 65.96 (OCH 2 CH 3 ),23.52(OCH 2 CH 3 ), 21.09 (NCCH 3 ), 18.89, 13.15 (CH 3 ) ppm.

Embodiment 2

[0027] The preparation of the iodide of β-diimine magnesium, the process is as follows:

[0028] In the absence of water and oxygen, 3.27 mmol of β-diimine ligand was dissolved in 25 mL of ether solution in a single-port reaction tube, and 3.60 mmol of methylmagnesium iodide was added dropwise to the above solution at -60°C, and reacted at room temperature for 15 h. After filtration, the solid was sucked dry, and the filtrate was concentrated to 5 mL to obtain colorless crystals. The mass of solid and crystals was 1.61 g, and the yield was 92%. M.p. 271-273°C. NMR spectrum: 1 HNMR (600MHz, C 6 D. 6 ):δ6.99-6.91(m,6H,Ar-H),4.88(s,1H,CH),3.12(s,4H,OCH 2 CH 3 ),2.65(s,6H,CH 3 ),2.08(s,6H,CH 3),1.55(s,6H,NCCH 3 ),0.48(s,6H,OCH 2 CH 3 ) ppm. 13 C{ 1 H}NMR (151MHz, C 6 D. 6 ):δ168.87 (NCCH 3 ), 147.75, 131.57, 129.56, 124.76 (Ar-C), 95.31 (=CH), 65.96 (OCH 2 CH 3 ),23.52(OCH 2 CH 3 ), 21.09 (NCCH 3 ), 18.89, 13.15 (CH 3 ) ppm.

Embodiment 3

[0030] The preparation of the iodide of β-diimine magnesium, the process is as follows:

[0031] In the absence of water and oxygen, 3.27 mmol of β-diimine ligand was dissolved in 25 mL of ether solution in a single-port reaction tube, and 3.27 mmol of methylmagnesium iodide was added dropwise to the above solution at -40°C, and reacted at room temperature for 15 h. After filtration, the solid was sucked dry, and the filtrate was concentrated to 5 mL to obtain colorless crystals. The mass of solid and crystals was 1.63 g, and the yield was 94%. M.p. 271-273°C. NMR spectrum: 1 HNMR (600MHz, C 6 D. 6 ):δ6.99-6.91(m,6H,Ar-H),4.88(s,1H,CH),3.12(s,4H,OCH 2 CH 3 ),2.65(s,6H,CH 3 ),2.08(s,6H,CH 3 ),1.55(s,6H,NCCH 3 ),0.48(s,6H,OCH 2 CH 3 ) ppm. 13 C{ 1 H}NMR (151MHz,C 6 D. 6 ):δ168.87 (NCCH 3 ), 147.75, 131.57, 129.56, 124.76 (Ar-C), 95.31 (=CH), 65.96 (OCH 2 CH 3 ),23.52(OCH 2 CH 3 ), 21.09 (NCCH 3 ), 18.89, 13.15 (CH 3 ) ppm.

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Abstract

The invention discloses a beta-diimide monovalent magnesium compound, a preparation method thereof and an application of the beta-diimide monovalent magnesium compound in hydroboration of aldehyde orketone. The preparation method comprises the following steps: under anhydrous and anaerobic conditions, a beta-diimine ligand reacts with a Grignard reagent, iodide of magnesium is generated and reduced by sodium, and a yellow crystal is obtained and is the beta-diimide monovalent magnesium compound. The beta-diimide monovalent magnesium compound is simple to synthesize, convenient to separate andpurify, clear in structure and high in yield; activity of the compound as a catalyst in catalysis of a reaction of aldehyde or ketone with pinacolborane is high, and the substrate universality is broad.

Description

technical field [0001] The invention relates to the technical field of preparation of metal-organic compounds, in particular to a β-diimine monovalent magnesium compound, a preparation method thereof and an application in hydroboration of aldehydes and ketones. Background technique [0002] It is well known that hydroboration is a very important reaction in catalytic reactions [Chong C.C., Kinjo R.ACSCatal.2015,5,3238; Geier S.J., Vogels C.M., Westcott S.A.ACS Symp.Ser.2016,1236,209.]. Although traditional transition metal catalysts have certain reactivity, they are relatively expensive, so it is imperative to replace traditional noble metal catalysts with other cheap catalysts [Vasilenko V., Blasius C.K., Wadepohl H., Gade L.H., Angew.Chem.Int . Ed. 2017, 56, 8393; Arévalo R., Vogels C.M., MacNeil G.A., Riera L., Péreza J., Westcott S.A. Dalton Trans. 2017, 46, 7750.]. Main group metals show obvious advantages because of their cheapness and environmental protection [Hill M...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F3/02B01J31/22C07C33/22C07C33/46C07C31/135C07C33/32C07C33/26C07C29/159C07C205/19C07C201/12C07C215/68C07C213/00C07D333/16C07C255/53C07C253/30C07C43/23C07C41/26C07C35/08
Inventor 马猛涛卢凯王未凡姚薇薇
Owner 厦门欧瑞捷生物科技有限公司
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