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Application of Tricene Rare Earth Metal Complexes in Catalyzing the Reaction of Aldehydes with Allylboronic Acid

A metal complex, allyl boronic acid technology, applied in the direction of organic compound/hydride/coordination complex catalyst, organic compound preparation, physical/chemical process catalyst, etc., can solve the problem of large amount of reaction catalyst and low reaction temperature and other problems, to achieve the effect of good universality, high reaction efficiency and simple post-processing

Active Publication Date: 2020-10-09
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, a class of chiral phosphoric acid catalyst (R)-TRIP-PA has been reported in the allylation reaction of allylic acid. In the previously reported allylation reaction system of catalyzed aldehydes, a large amount of reaction catalyst is generally used. , low reaction temperature and many other harsh conditions

Method used

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  • Application of Tricene Rare Earth Metal Complexes in Catalyzing the Reaction of Aldehydes with Allylboronic Acid
  • Application of Tricene Rare Earth Metal Complexes in Catalyzing the Reaction of Aldehydes with Allylboronic Acid
  • Application of Tricene Rare Earth Metal Complexes in Catalyzing the Reaction of Aldehydes with Allylboronic Acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: La(Cp) 3 Catalyzed Reaction of Benzaldehyde with Allylboronic Acid

[0024] Add 0.0004 g of catalyst La(Cp) to the reaction flask after dehydration and deoxygenation treatment 3 (0.1% molar dosage), then add 0.081 mL benzaldehyde with a syringe, dissolve the catalyst, mix well, then add 0.180 mL allylboronic acid with a syringe, stir the mixture at room temperature, react for 1 h, and expose to the air to terminate the reaction , add 8 mL of 1 M HCl solution to hydrolyze the product, separate by column chromatography (ethyl acetate: n-hexane = 1:10) and purify to obtain the corresponding allyl alcohol (1-phenyl-3-ene butanol) , NMR yield 99%, separation yield 91%. NMR data of the product: 1 H NMR (CDCl 3 , 400 MHz): δ 7.34-7.20 (m, 5H), 5.85-5.71 (m, 1H), 5.16-5.10 (m, 2H),4.72 (dd, J = 7.6, 5.6 Hz, 1H), 2.54-2.43 (m, 2H), 2.00 (br s, 1H).

Embodiment 2

[0025] Embodiment 2: Nd(Cp) 3 Catalyzed Reaction of Benzaldehyde with Allylboronic Acid

[0026] Add 0.0004 g catalyst Nd(Cp) 3 (0.1% molar dosage), then add 0.081 mL benzaldehyde with a syringe, dissolve the catalyst, mix well, then add 0.180 mL allylboronic acid with a syringe, stir the mixture at room temperature, react for 1 h, and expose to the air to terminate the reaction , add 8 mL of 1 M HCl solution to hydrolyze the product, separate by column chromatography (ethyl acetate: n-hexane = 1:10) and purify to obtain the corresponding allyl alcohol (1-phenyl-3-ene butanol) , NMR yield 99%, separation yield 90%. The NMR data of the product are the same as in Example 1.

Embodiment 3

[0027] Embodiment three: Sm(Cp) 3 Catalyzed Reaction of Benzaldehyde with Allylboronic Acid

[0028] Add 0.0004 g catalyst Sm(Cp) to the reaction flask after dehydration and deoxygenation treatment 3 (0.1% molar dosage), then add 0.081 mL benzaldehyde with a syringe, dissolve the catalyst, mix well, then add 0.180 mL allylboronic acid with a syringe, stir the mixture at room temperature, react for 1 h, and expose to the air to terminate the reaction , add 8 mL of 1 M HCl solution to hydrolyze the product, separate by column chromatography (ethyl acetate: n-hexane = 1:10) and purify to obtain the corresponding allyl alcohol (1-phenyl-3-ene butanol) , NMR yield 98%, separation yield 89%. The NMR data of the product are the same as in Example 1.

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Abstract

The invention discloses the application of a tricene rare-earth metal complex in catalyzing the reaction of aldehyde and allyl boric acid. Allyl alcohol is prepared by using the aldehyde and allyl boric acid as raw materials and the tricene rare-earth metal complex as a catalyst. While the reaction conditions are mild and the catalytic activity is improved, the preparation difficulty of the catalyst itself is reduced, and the post-processing cost is reduced.

Description

technical field [0001] The invention relates to an application technology of a metal organic complex, in particular to the application of a tricene rare earth metal complex in catalyzing the borylation reaction of aldehyde and allylboronic acid. Background technique [0002] Allyl alcohol is an important intermediate in organic synthesis, and has a very wide range of functions in the synthesis of many medicines and fine products (Keck, G E.; Covel, J. A.; Schiff. T; Tao, Y. Org. Lett . 2002, 4 , 1189). Among various methods for preparing allyl alcohol, allylation of aldehydes is a relatively mature and effective method. At present, the studies on carbonyl allylation mainly focus on substrate-induced and chiral catalyst-catalyzed asymmetric allylation of aldehydes. In terms of substrate induction, various allyl silicon reagents have been developed, but their practical application is severely limited due to the low activity of silicon reagents. Samir et al. also used the l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/38C07C33/03B01J31/22
CPCC07C29/38B01J31/2295B01J2531/37B01J2531/38B01J2531/0225C07C33/03
Inventor 薛明强朱章野颜丹丹陈素芳洪玉标沈琪
Owner SUZHOU UNIV